To say 2023 was one for the books would be like saying Uncle Jesse is mildly cute.
Uncle Jesse.
The year started with an epic heart break and multiple health scares (to the tune of $7,000 and counting, no less), a trip to the E.R. with my bestie, and sending out 304 job applications, which resulted in six interviews, three job offers, and two recinded job offers (based on last minute organizational changes).
It also involved going out with 36 different men.
And thus, I give you, my 2023 Dating Year in Review (if the embedded video doesn’t play, you can watch it here):
Disclaimer: This blog post is memoir. It reflects the author’s present recollections of experiences over time. Some names and characteristics have been omitted or changed, some events have been compressed, and some dialogue has been recreated.
“Are you ‘Straight As Double Ds’?”
The three of us looked up from our table to see a tall, smiling, 30-something-ish man standing over us.
“We are!” Erin, Michelle and I exclaimed, delighted that this cute, normal-seeming guy recognized us by our trivia team name.
Team Straight As Double Ds in action: My usefulness finally kicks in on a “Sandwiches” round.
“I was at trivia last night on [the winning team]!” he laughed, explaining how he recognized us.
“Booooo!” we teased.
“No fair – you have a ringer on your team!” I added.
We bantered back and forth for a minute and Erin kicked me hard under the table. Not an hour earlier, the three of us had been describing our Dream Men. Despite being close friends in our early 40s who’d all been through the dating gauntlet in our small, central Oregon town (including dating the same guy), we’d never had that conversation before.
“Well apparently I like tall, bald guys,” I had joked, referring to the last guy I’d fallen for. “I just want him to be kind and funny.”
Our newest fan club member uncannily fit the bill on all fronts. He introduced himself as Fred and we liked his unassuming nature so much that we found ourselves saying,
“Come sit with us!”
It was Wednesday karaoke night at a downtown dive bar, and while we’d normally be in bed by that hour on a weeknight, it had been an emotionally charged evening and we had decided we needed a little more time together.
“Why did you kick me under the table?” I asked Erin the first chance I got.
“Because that’s your boyfriend!” she squealed.
My gut immediately told me she might be right, but I also resisted.
“Did you see his phone!? It looks like a burner phone! There’s no way.”
Fred went on to boldly sing two rap songs, further wooing us with his unabashed performances.
Although no one can top the Legendary Erin.
“I’m from Jersey,” I explained to Fred near the end of the night, at which point he pulled out his [ancient burner] phone to show me his favorite Jersey Shore meme.
“Oh my god, you have to send me that!” I exclaimed by way of getting his number.
I insisted on also trading last names.
“We met in person so we should be on the up and up,” I said. “But don’t Google me.”
We both proceeded to immediately Google stalk each other and, seeing that he had no criminal record (because that’s a thing that happens way too often), I invited him to another, more mellow karaoke night with my entire family (who were about to visit from New Jersey) a few days later.
Fred arrived to Karaoke Night Reloaded on the early side and seemed nervous. He charmed everyone with his sincerity, sweetness, and eye-wateringly off-key rendition of “Buddy Holly” by Weezer. By the time we ended the night at a 90s Dance Party, we slow danced and confirmed a mutual spark.
Attempting to look “tough” during a 90s dance party at the yuppiest spot in town.
I tried to temper my excitement. After four years of dating in central Oregon, I’d finally deleted the apps (Bumble and Hinge) two months earlier – for good.
“Do you want to see Sylvan Esso with some friends and me on Sunday? Tickets are down to $18!” I texted Fred the following week.
He replied with a screenshot showing his ticket purchase confirmation. I like his style.
“Do you want to meet before the concert for a one-on-one drink?” I asked.
“Is this a date?” he clarified and I confirmed.
When date night arrived, I was nervous. Really nervous. Despite having spent two nights together during which he met most of my friends and family, now a feeling of expectation permeated the air.
“It’s really hot out and I’m going to assume you don’t mind that I’ve opted for less clothing,” I teased.
#shamelessselfienumber1467
With two minutes to spare, I pulled into the agreed upon parking lot and saw Fred tearing ass down the sidewalk towards the bar where we were meeting, clearly terrified that he’d be late. I laughed out loud and, as soon as I parked, texted him.
“Don’t run! I just parked!”
“Okay I won’t,” he answered, not catching on that I’d seen him running.
He offered to buy our drinks and when I said I liked bubbly, he looked confused.
“What does that mean?”
“Like champagne, sparkling wine.”
“They have that here?”
“Yeah, only one kind.”
“So I just ask for ‘bubbly’?”
I tried not to giggle and nodded. We awkwardly picked a spot to sit down and I hoped that a couple of drinks would soothe our collective nerves.
“So… I live with my parents,” he blurted almost as soon as we sat down.
“Yeah, I know,” I replied.
“You did do your homework,” he said. “And you still showed up. That’s good news for me. I’m really only now getting to a point where I feel comfortable going out and spending any money.”
He went on to briefly explain his situation and it was as I’d suspected. Crappy jobs, no jobs, and bam. Living with the parents. For years. Up until that point, I never would have considered dating a middle-aged man who lived with his parents due solely to financial troubles, but he seemed so genuinely kind that I felt like I had to give it a chance.
“Financial situations can change,” I explained to friends, “but character doesn’t.”
My friends and family, knowing how much I struggled to find a partner who was pure-hearted, stable, and emotionally available, supported my decision to see where this might go.
Grocery receipt or list of dating disasters? You decide.
Fred and I were feeling a lot looser by the time we walked over to the concert, and when the sun began to set, we wrapped ourselves up in each other, swaying to the mellow, dance-y beats.
When the lead singer’s 50-foot tall image appeared on screen in a tight jumpsuit, Fred said in my ear,
“That’s not a very flattering outfit.”
I drew my head back and pulled away, looking at him with furrowed eyebrows.
“What?” he replied, his expression dropping.
“I think she looks amazing.”
“I didn’t mean anything by it! I was just saying it’s not the most flattering outfit! What, I’m not allowed to say that?”
We parted ways for a couple of minutes while I tried to figure out if I was overreacting.
“Sorry,” I said, touching his shoulder. “I just don’t like people commenting on other people’s bodies. Especially men commenting on women.”
“I thought I blew it,” he said, looking relieved.
“Man, I should have shaved my knees!” I joked a little while later, realizing my knees and thighs were visible in my mesh dress.
“I am NOT into hairy legs,” Fred immediately retorted. “I like fully waxed.”
Again I drew my head back as my stomach sank. I had flashbacks of the Navy pilot and the guy who asked for his key back – the two boyfriends I had in 2014 right after my divorce, back-to-back, who both had more than a few red flags. One of the first signs was commenting on other women’s bodies, positively or negatively. At the time, I didn’t have the vocabulary to articulate what my gut was telling me, but nine years later, alarm bells rang loudly: NEXT HE’LL TELL YOU HE HAS MOMMY ISSUES. RUNNNNN.
“What? I’m not allowed to have a preference?!” Fred argued.
Later, in the parking lot by our cars, I had the opportunity to explain where I was coming from.
“When you judge other people’s appearances, I take it personally and assume you’ll say the same unkind things about me. I also don’t think it’s anyone’s business or place. My body is the least interesting thing about me.”
Having lost and gained so much weight since childhood, struggling with binge eating (which I had told him about over drinks earlier), I had grown to have zero tolerance for body shaming or judgment of any kind.
And if that doesn’t work for you, you can fuck right off.
He apologized and said he understood. I felt comforted, believing he was just inexperienced but willing to learn and grow. Cue: an intense, long make-out session until a security guard came over.
“You can have ten more minutes before I have to kick you out,” the security guard said, realizing we weren’t stealing anything besides smooches.
When Fred and I had our second date two nights later, the body grooming topic came up again.
“I’m sure there are preferences you have, too!” Fred insisted. “Like I’m sure you’d prefer I had hair and didn’t live with my parents.”
I said nothing because, unlike Fred, I knew when to keep my mouth shut.
“If you want to get anywhere with me,” I explained, “your job is to build me up and make me feel like the most beautiful woman in the world, no matter what.”
By then he’d already made a number of sexually forward comments and I couldn’t help but wonder if he got all of his “preferences” from porn. Right before the end of the night, the topic of children somehow came up.
“Wait, do you want kids?” I asked, taken aback. “Because I’m 41 and I have an IUD.”
“I mean I know we’re basically the same age, but I’m still open to it. I could always date someone younger.”
Though he hadn’t said it pointedly, I couldn’t help but bristle.
Me contemplating how to acquire the confidence of a white, middle-aged man.
“I just don’t want us to waste each other’s time,” I answered.
He assured me it wasn’t a dealbreaker.
A few days later, Fred picked me up for a third date, putting in the effort to hold open doors, buy me a small present, and pay for my ticket to a beer tasting event. I still wasn’t sure how I felt; the “nice guy” I thought I’d met definitely had some chinks in his armor. …But were they really gamestoppers?
After all, we did have fun together.
“I can get angry sometimes, and I don’t want you to see that part of me,” he had texted the night before. “I can get mean, and my parents and I get into yelling matches sometimes.”
The text had come out of the blue and while it had made me incredibly uneasy, I decided not to jump to conclusions.
“Do you mean angry like ‘even medication doesn’t help’ or angry like, ‘I’m frustrated with life and the world is on fire’ [like the rest of us]?”
“I’m not on medication. I’m just afraid for the moment when you realize I’m not perfect.”
Oh lord, Fred. We are way past that.
“Well, if I haven’t scared you off yet, I really think we should give this a shot,” Fred ended the conversation.
The exchange played through my head as we entered the beer tasting event. Between that and knowing I was about to meet his parents, I was on edge. When we handed over our tickets, I learned that we still needed tasting tokens – the cheap tickets Fred had purchased only got us into the event.
Fail.
“How much are they? For how many? And what does that get you?” Fred asked a series of questions to the token seller while I slowly died inside.
“I’ve got it,” I intervened and bought us enough tokens to cover a solid handful of tastings each.
We started the night out by bumping into a couple of guys from his trivia team who made several tasting recommendations.
“Oh hey, let’s try this beer!” Fred exclaimed a little while later, walking over to one of the booths.
“I’d never heard of this one,” I said. Before I could add, ‘Until your friends mentioned it tonight,’ he cut me off.
“[My friends] literally just told us about it.”
I pursed my lips. “I know, I mean I had never heard of it before then.”
Fred got drunk quickly and started trying to tip the vendors with tokens.
“Keep it, man,” one seller explained, eyeing him dubiously. “We can’t cash them in for money at the end of the night so you’re just wasting a token.”
Yeah, Fred. The tokens I bought.
“No, no, you take it,” Fred insisted over and over, clearly too buzzed to understand the concept that wooden tokens did not equal tip currency in Beer Tasting World.
Perhaps I should have been charmed by the attempt to tip in tokens, but I was too turned off by his refusal to listen to a simple explanation – a pattern that would only progress as the night wore on.
So many fails, so little time.
“Oh hey, there are some of my gaming buddies! Can we go say hi?!” Fred said, making a beeline towards two men before I had the chance to answer.
A little while later, his parents walked over. They were put together, aside from being tipsy, but didn’t seem especially keen on chatting, which struck me as odd. Were they not curious about the winsome blonde their son had wrangled? Fred immediately ignored us in favor of continuing his conversation with a friend, so I was left on my own to show them what a catch I was.
Did I mention I have a 401k and multiple house plants?!
“[Fred’s dad and I] met at a roller rink!” his mom told me.
“Oh my god, no way! Tell me everything!”
For the next half hour, I played the role of Charming Girlfriend while Fred talked only to his friend.
I tried not to peek at my watch. It was official; I was not having fun. As the event neared closing time, I decided we needed to eat. Knowing how broke Fred was, I offered,
“Hey, I’m starving, how about I make us a pizza at my place?”
I had spent half the day –after an insanely busy and stressful month of job interviews, social commitments, visitors, freelance work, a broken toe, a broken phone, and a flat tire– cleaning and grooming in preparation for this date. I was hellbent on salvaging the night.
After pizza and a walk down memory lane reminiscing about our first concerts, a heavy make-out session ensued, my back pressed against the refrigerator. Maybe this can work… I pulled back and looked at him.
“So,” I began. “Are you prepared if things do get intimate between us?” I didn’t have any intention of sleeping with him that night, but I wanted to know where we stood.
“Don’t you have an IUD?”
“Yeah…but that doesn’t protect against STDs…”
“Well I don’t have condoms,” Fred replied. “But I’m good to go.”
I raised my eyebrows and he continued.
“I mean I haven’t had symptoms of anything in the past two months which is what the guidelines say.”
“Um, I don’t think that’s how it works,” I replied.
“Well if you want to go against what the research says…” Fred said before going on in great detail about his dating and sexual history.
“My last ‘real’ relationship was for a few months in 2018,” he rambled. “with a woman a few years older with kids. Like you, she pursued me.” I tried not to make a face as he continued. “We were gonna move in together and I was cool with taking on the kids, but then she said she felt like she was holding me back from my gaming dreams. I thought that was so nice of her. I wanted to stay together, but she was so awesome to not want to hold me back.”
Oh holy fuck, Fred, really? That woman was trying to get rid of your ass without drama!
“I know. I know. This is really how men interpret us.”
He went on about one other “really nice” woman who was “there for him during the pandemic” until I held up a hand.
“I don’t need or want to know any of this. I just need to know that you’ve been tested.”
“I could ask you the same question!” he said accusingly. “Have you had sex with anyone since your last doctor’s visit?”
“No, I haven’t.”
“Okay, so you’re good. I’ll go out and buy condoms right now!”
How could I explain that he was missing the point? On top of being willing to put both of us at risk, he was clearly demonstrating a lack of safety, care, and maturity.
The conversation turned into a full-blown argument until I said calmly,
“You’re raising your voice. It’s late. I have neighbors. You said you had anger issues and I’m just trying to suss some things out here.”
“Now you’re spinning my words! How could you think I’d be so open with you and then put you in any kind of danger?!” he cried, seeming to still think he could convince me to have unprotected sex. I’d never wanted anything less in my life. “I don’t like being analyzed!”
“What I was hoping you would have said when I asked if you were prepared,” I took a deep breath, “was, ‘Of course. I’m happy to do whatever you need to feel comfortable, Jules.'”
“Oh, well, I’m sorry I didn’t say EXACTLY the perfect thing!” Fred spit back.
I started cleaning up the kitchen, talking more to myself than him.
“Look around, Fred. I’m a grown-up with a grown-up life. This is a normal conversation to be having when you’re starting a new relationship. How do I keep getting myself into these insane situations?”
Fred sat at the bar overlooking the kitchen sink where I was washing dishes and replied, “Now you’re just being condescending!”
“You’re right. That’s what I do when I’m pushed to my limit.”
“Fine, I mean I guess if I have to go through all of that…”
“All of what?” I asked.
“Getting tested.”
“Oh, so I’m expected to go through all of the pain and money and time of getting fully waxed on a regular basis, but you can’t go get tested ONCE?!”
I knew that would set him off anew, but I was done. He ranted and raved until I said what I should have said an hour earlier, or perhaps a week earlier,
“You need to leave.”
While he put on his coat and shoes, I went into the bedroom to snuggle Uncle Jesse (Doodle Wonder Dog) and calm my nerves. I was proud of myself for not exploding or hitting below the belt.
I came back out into the living room when I heard the front door open. Fred was staring at me with puppy dog eyes.
“I’m sorry, I hope we can still work this out. Thank you for the drinks and everything tonight.”
“Okay,” was all I could muster, eagerly locking the door and turning off the porch light as soon as he left.
I laid in bed wondering if there was any chance I had overreacted. No. This was genuinely fucked. Glad I know now, I texted to friends.
The next day, I visited Michelle at a local market where she had a booth selling her (stunning) jewelry. Another friend, Margaret, bumped into us and I told them both the latest drama.
The reviews are in and it’s two a billion thumbs down, Fred.
“Wait, Fred who?” Margaret stopped me mid-sentence, putting a hand on my forearm.
My stomach dropped.
“Fred Cooper.”
“Does he have asthma? And does delivery for that pizza place?”
“Yes!”
“Jules, I know him! He came up to me like two weeks ago at a fair and chatted me up! He asked for my number! But then I lost my phone so I chalked it up to a missed connection!”
“Oh my god!” I slapped my forehead. “He acts like he’s so innocent and doesn’t date!”
“He seemed really nice!”
“Yeah, he does seem really nice.”
“God. I can’t believe that happened to you last night. I’m so sorry. That’s messed up!”
The entire day passed without a word from Fred. The following morning at precisely 11:11am, he texted,
“Jules I’m sorry about the other night. I’m not sure why I responded the way I did. I hope we can talk this through because you do mean a lot to me.”
I had one tiny moment of self-doubt before coming to my senses. I archived our message thread and said a prayer of thanks for having my head on straight and my heart intact through this one.
They’re everywhere, Fred. You don’t even need a wooden token.
Disclaimer: This blog post is memoir. It reflects the author’s present recollections of experiences over time. Names and characteristics have been omitted or changed, some events have been compressed, and some dialogue has been recreated.
~*~*~*~*~*~
“So why didn’t you move things over to text message?” Sam asked about an hour into our first date.
We’d connected on Bumble a couple of weeks earlier and finally gotten the chance to meet for a drink. We sat in oversized chairs in front of an even more oversized fireplace, my left leg growing hot from its proximity to the raging flames. I kept catching myself thinking, ‘Is my skin really that pale?’ as I stared at my bent knee, my foot resting on the giant concrete hearth. I could see my snowy white flesh, nearly translucent, through one of the deliberate tears in my overalls.
I call them my emotional support overalls and wear them whenever I have to talk to single men.
Sam was 54 (to my 40) and, from his photos, a very young 54, skiing, surfing, and smiling in every picture. The Sam who walked through the bar doors was definitely 54, though dressed youthfully and sporting a playful grin. Throughout the first hour, he kept tapping my arm or leg whenever I said something funny and I decided I did not like that, thankyouverymuch.
“Well, I usually don’t give out my number until I’ve met someone in person,” I explained, wondering how on earth this man hadn’t caught on to that Online Dating Standard Operating Procedure.
His question had come out of the blue. I wouldn’t have even remembered that he’d sent his number except that I had just reread our entire (brief) Bumble chat history before meeting up as a refresher. He hadn’t expressed any concern about it at the time and I figured he understood that that was outside of my comfort zone.
“Really?” he pressed. “I always do and I’ve never had anyone say that.”
I furrowed my brows. “My friends and I almost always wait to give out our numbers. Once you meet and see if there’s a connection.”
“Why?”
I almost laughed in disbelief. “Wellllll….have you ever heard that [Margaret Atwood] quote about how men’s greatest fear of women is being laughed at, and women’s greatest fear of men is being murdered?”
“Have you ever had anything scary happen?” he asked skeptically, angling his body farther away from me. “I haven’t.”
“I know for a fact none of my friends are murderers.”
I resisted the urge to scoff. Well there you have it, judge and jury. None of the men in this guy’s life are known murderers. They must not exist and I’m just overreacting.
“The men who kill their partners or exes are beloved friends, coworkers, neighbors… Love and unrequited love situations can result in even a ‘nice guy’ doing very bad things.” I didn’t bother telling him about my personal proof. Or about how the leading cause of death in pregnant women in the U.S. was HOMICIDE. He wasn’t listening.
“Well, I don’t think it’s a big deal. Besides, I have better things to do with my time than blow up someone’s phone who’s not interested,” he replied, bristling just slightly.
I nodded, noting that our entire dynamic had shifted. He’d mentioned being liberal and earning a Masters degree from a very prestigious east coast university. Apparently they didn’t cover Obvious Facts and Topics to Debate, Um, How About Never, Let Alone on a First Date with an Internet Stranger.
“Well, I should probably go check on my dog,” I said in a chipper voice a few minutes later, trying not to sound too obvious that I was just trying to get the hell out of there. I was proud of myself for not doing my usual, ‘Let me get the next round’ bit in an effort to be polite and salvage the evening. I had bumped into a few friends at the bar and decided I’d walk out with Sam and double back to hang out with them, beyond caring if he realized that that was my intent.
“Nice to meet you and talk soon,” Sam said briskly, giving me a quick hug outside before taking off towards the back parking lot. The tone in his voice let me know I probably didn’t have to worry that he’d be in touch.
What the actual f$@%, I thought as I walked back into the bar to join my friends. How did that man hit 54 and not learn about Dating Safety 101?
“Ya gotta try younger guys,” I had started to regularly joke with my single girlfriends. “They are so fun and woke and sensitive.”
By and large, any time I’d tried dating older men, especially a decade or more older, it went very poorly. Also, why didn’t this dude just drop it? I thought back to my other date that week, Neil, a 43-year-old father. It had been a second date and the moment he’d walked in to play trivia with me, wide-eyed and easily distracted, I’d known we weren’t a match. When I texted to politely tell him I wasn’t interested in a third date (after he had suggested a plan), he replied,
“I agree we aren’t an obvious match but I felt there was enough there to explore more. […] I’d love one more chance to see if there’s anything there.”
Turning someone down once is awkward enough; now I had to do it twice? And how could two people have had such a different experience of the same night?
The older I get, the more I realize how subjective our individual experiences are. AND IT’S FORKING TERRIFYING. Here’s a palate-cleansing photo to help ease the terror.
Sam’s ignorance about domestic violence and Neil’s persistence were hardly the most unsettling dating experiences this year (…and it’s only March).
“Damn, you still look marvelous.”
When Paul reached out on Hinge two months ago, I rolled my eyes and replied,
“hahaha hey Paul. Say hello to my friend Rachel the next time you two hang out. I’m looking for something serious, but thanks for the compliment!”
Paul and I had gone out a couple of times in late 2021, making out and making plans to see each other a third time. He flaked more than once and I finally wrote him off, my feelings hurt. Fast forward six months later and he matched with my friend, Rachel.
“Go for it,” I said when she showed me his profile. She didn’t realize I knew him and was simply asking if she should go on a date with a younger guy. I told her about our brief history and added, “He’s a nice guy, you’ll be safe. And if you’re looking for something casual, he fits the bill.”
They wound up hanging out a number of times and I realized it was, in fact, kinda awkward. Moving from New Jersey to central Oregon was eye-opening in many ways, especially in terms of small town dating. It was all starting to feel…incestuous. So when Paul again reached out via text a month later, I wasn’t entirely surprised.
“I’m curious to explore things with you,” he texted. “I know previously the timing/availability for me didn’t line up and I’d very much understand if that door is closed for you. If it isn’t fully closed, I’d love to meet up sometime soon to reconnect.”
I wasn’t planning to reply, but when my friends saw the text, they unanimously urged,
“You should give it another try! That’s a great message! You liked him before, right?”
“That was a long time ago,” I said. Sure, he was a nice enough guy, but I’d been through a lot over the past year and a half and had learned much more about who and what worked for me. A sober, quirky, 29-year-old rock climber probably wasn’t going to cut it. “But okay, fine.”
“That depends,” I wrote to Paul. “How many vegan dinners are you prepared to buy me?”
Yes, I can be bought.
We texted quite a bit after that and Paul assured me he was earnest in now wanting something more serious in his life. When we met for dinner a week and a half later, he did indeed pay, but also interrupted me countless times while we talked about our careers for three hours. I wasn’t sure if it was a date or a networking session, but nevertheless, the time did pass quickly.
“The energy between us feels much different this time around,” Paul said. “Much more calm.”
“Huh,” I replied, nodding, trying to remember the specific vibe of our earlier dates. “I guess I was in a much different head space then. Yeah. You’re right.”
“So can I see you again? Can we make a plan right now? How about Friday?” he asked once we were outside saying goodnight.
I was always impressed when men boldly showed their interest through making rock solid plans. I found myself agreeing.
“Sure, yeah, I think I’m free on Friday.”
For our second date, we met at a Thai restaurant and Paul was late. As soon as he sat down, my body had a visceral reaction. Oh hell no. He had a huge, flaky piece of skin on his lower lip and with the natural light flooding through the floor to ceiling windows, I could see his teeth were yellow and plaque-covered.
Dental hygiene. It’s my top thing. Besides wine and not getting murdered.
For the next hour and a half, I let Paul dominate the conversation and finish all of my food, occasionally dropping suggestive comments.
“That skirt is really short. I love it.”
I tried not to grimace and changed the subject.
“So do you think you can get past the fact that I’ve hung out with Rachel?” he asked towards the end of dinner. I stared him dead in the eye.
“I don’t know. Honestly, I’m a little butt hurt that you stuck your tongue down my throat and then ghosted, and went on to hang out with my friend regularly.”
Paul looked embarrassed and tried to deflect. “Yeah, but who sent the last text message [between us back in 2021]?”
“I don’t know! Wait. Okay, so it was you, but you totally blew me off! You kept saying you were busy or sick.”
Paul chuckled sheepishly. “Yeah, okay, that was a weird time for me. I was kind of going through a ho phase.”
He continued to pepper in flirty comments and I knew in my gut it wasn’t just a phase. When the bill arrived, I grabbed it and insisted on paying, my way of closing the door completely to…whatever this was.
“What should we do next?” Paul asked. I had already been rehearsing my reply in my head.
“I’m going to go hang out with my friends,” I said bluntly. He knew they were also downtown at a nearby bar and I couldn’t wait to get to them.
“No problem,” he replied, to his credit, gracefully. “I’m exhausted so I’ll probably just head home.”
“I’d love to do this again soon,” he said when he hugged me goodbye.
“Yeah… Have a good night!” I replied, taking off in the opposite direction.
“WHAT WAS I THINKING,” I blurted as soon as I was surrounded by my beloved gal pals. We were all squished in a cozy corner at an upscale bar and I felt like myself again.
Gal Pals: the only remedy to online dating.
I’d chalked Paul Round #2 up to an ego boost, but later that weekend, I realized it was much deeper than that. I had wanted to believe that I wouldn’t have just made out with, and gotten slightly hung up on, a guy with whom I didn’t have a genuine connection. Meeting Paul in 2023 was an attempt to prove that we clicked and I was pursuing something real, not casual. Anything else -though it can work well for others- would have been in conflict with the vision I held of myself.
But Paul wasn’t a match. Far from it. Nor was Neil. Or Sam. Older, younger, my age, it didn’t really matter; they just weren’t right for me. And that was okay. Maybe soon I wouldn’t agree to second dates, let myself be interrupted, offer my meal, or debate open-and-shut topics with wildly incompatible men.
Maybe in knowing myself just a little bit more with each bad date and heartbreak, I was getting closer to finding the person worth my time and energy.
Disclaimer: This blog post is memoir. It reflects the author’s present recollections of experiences over time. Some names and characteristics have been omitted or changed, some events have been compressed, and some dialogue has been recreated.
~*~*~*~*~*~
Can I cancel? I really want to cancel.
I stared at the clock. It was 4:30pm, a.k.a. Online Dating Witching Hour, when single, 40-year-old women’s nervous systems kick into high gear and Fight-or-Flight battles with Reason.
I was feeling especially cagey about that night’s first date because, just the night before, I’d gone on a first date that went disturbingly sideways. While it initially seemed like a great conversation with someone who might make a wonderful friend, the guy got drunk, propositioned me, and then backpedaled by explaining that he “understood women” because he “had daughters” and, for example, knew I had taken my purse to the bathroom “because I had had [my] period.”
Spotted him again on Hinge last week. He now lies about his first name AND his age. Get in line, ladies!
Fast forward 24 hours and the internal debate raged on. Doooon’t cancel. You know how bad that feels when it happens to you. Plus, this is a midwest guy. He’s not going to talk about periods.
David and I had matched on Bumble about a week and a half earlier and he immediately explained that he was en route to Bend to spend Christmas with his dad, splitting his time between Bend and the midwest.
“I moved to [the midwest] about 7 years ago,” David wrote in his first message to me. “With my no [sic] ex-wife. When we separated I have been spending more time out in Bend with my Dad. Love both places.”
“I read that a few times,” I wrote back, “asking myself, ‘Oh lord, what is a no ex wife? Is this another ethically non monogamous dude?’ and then realized you probably meant ‘now ex wife’? …Correct? (You can never be too careful on these apps.)”
“haha yes, I did. I saw that after it was too late. But I hear ya, I’ve noticed a lot of that on here – I’m definitely not that.”
I suggested we meet at one of my favorite casual restaurants downtown for a drink when he got to Bend, and when our date night arrived, I decided NOT to cancel and dress up in a black top and skirt.
David walked in ten minutes late looking a little flustered, having gone to the wrong spot in the sprawling restaurant. He was tall and dressed like a midwest-meets-Bend hipster: plaid shirt, vest, wool beanie.
“Are you a hugger?” I asked, rising to greet him with a smile.
“Absolutely, yes,” he said and hugged me in a way that showed he meant it.
Well, he’s definitely cute, I thought as we took our seats. He hadn’t been smiling in any of his dating profile photos and I was pleasantly surprised to see how charming he looked when he did, which was often and easily, just like me. The conversation started slowly and I struggled to get us away from mundane small talk. I bet he’s bored out of his mind and can’t wait to leave.
“So this is actually my first ever online date,” David confessed.
“THAT IS NOT FAIR,” I immediately blurted.
“I just had a good feeling about you,” he shrugged.
“You hit the jackpot,” I teased. “That really isn’t fair.”
When we finished our second drink, I was surprised that David both insisted on paying (a growing rarity in the online dating world) and then said,
“Should we get another somewhere else?”
I suggested a nearby bar and as we made the short walk, I cautioned,
“I’ll need a chivalrous arm because the entire parking lot is a sheet of ice.”
He offered his right arm and I got the sense that that one small gesture healed something inside both of us. We ordered whiskey cocktails -he again insisted on paying in an easy, swoon-worthy way- and we settled into a more intimate, relaxed conversation, diving into topics like veganism, financial security, and, of course, cheesecake.
“I’ve been wanting to try to make a vegan cheesecake now that I know all of the best vegan dairy products. I could make you one for your [upcoming] birthday if you’ll be in Bend!”
“I could be in Bend for my birthday,” he replied without hesitation. He made several similar comments that night that had me feeling confident I didn’t have to worry that he owned a house 2,500 miles away.
“So what are you looking for?” he asked at one point.
“A partner,” I replied immediately and he nodded, seeming not the slightest bit surprised.
“I’m beginning to see that you really need this,” he teased at the end of the night, seeming much more at ease, as he again offered his chivalrous arm all the way back to my car. This time, the insanely icy sidewalks almost took us both out.
In Bend, snow management = There’s snow. You’ll manage.
“So how does this work? Do we exchange numbers?” he asked once we reached my car. I nearly melted at his naïveté. He took out his phone and I gave him my number.
We texted until midnight and all I could think was: This guy is out of my leagueand I NEED TO LOCK. IT. DOWN. Smart, handsome, polite, artistic, sensitive, financially secure, active, a dog lover and foodie… He spent his free time doing creative and varied hobbies and had built a community and life for himself that mirrored what I had in Bend. He was even left-handed like me, and it didn’t hurt that his teeth were perfect and he smelled great, too.
“So are we calling today our first date or is it just the Crazy Vetting one?” I texted.
“Well, whatever you call it I liked it and I want more.”
“I learned from true crime shows that once you let them take you to a second location…it becomes a first date.”
“Call it what you want so long as I get to take you on another date.”
“Looking forward to gripping your manly chivalrous arm next week [when I get back from a Christmas trip].”
“I look forward to that, too. I still have a moment I am thinking about when I was just looking into your eyes and thought, ‘huh, this girl is hanging out with me? That feels really nice.’ Just a simple acknowledgement, and appreciate that, wherever it goes from here.”
The next day, on the long drive to the Oregon coast with my “Bend sister,” Erin, I immediately warned her,
“I’m not going to be able to shut up about David, so should I just get it all out now?”
She laughed and let me ramble about all things Amazing David for at least an hour.
“He remodeled his kitchen himself – and it’s my dream kitchen! He taps his own maple trees! He paints! He sails! He plays hockey! He does yoga! He said he’s working on a cookbook with mostly vegan recipes! …I should probably try to go on a date on the coast just so I don’t get too obsessive.”
It was a tactic I’d picked up from a respected friend (now married via Tinder): always keep 4-5 guys in the rotation in the beginning so you don’t get too hung up when one doesn’t text (or winds up claiming he has an alien blood type). This adopted strategy kept me from texting David a ton over the following few days, although we did exchange several messages each day.
I mean obviously he needed to see this photo.
“Do you mind if we play things by ear on Monday? I might be wiped when we get back,” I texted. I was eager to see him, but wanted to bring my A game. He assured me he’d make himself available whenever I was free.
On Monday, I decided I couldn’t wait another moment to see him and we arranged to meet at a nearby, mellow restaurant with lots of vegan options. This time he was only a minute or two late, and when he walked in, my face exploded into a wide grin.
“Hi,” he said, smiling from ear to ear. His eyes sparkled and I could feel his expression reflected in my own. He looks SO happy to see me. We hugged and everything felt warm. Good. Right. Conversation flowed and we shared a giant salad with tempeh and vegan wasabi mayo – a combination we both couldn’t get enough of.
“Did you know they don’t use real wasabi in the U.S. because it’s too expensive?” David asked. “It’s actually just horseradish.”
“Are you serious?” I replied. “What is real wasabi then?”
“It’s a plant in the radish family that only grows in Japan.”
Marry me.
“Holy crap it’s already almost nine,” I said later, the past three hours having flown by. “Excuse me, I’m going to use the restroom before they close.”
When I came back, we chatted some more and I wondered why no one was bringing the check. The waitstaff was already putting chairs up.
“I guess we should get the bill?” I finally said.
“Oh, I paid when you were in the bathroom,” David explained.
Marry me.
As we walked outside, I was struck by how small I felt next to him – not a common feeling at 5’8″. We stood in front of my car silently for a moment, his eyes glowing. He leaned forward and placed the most gentle kiss on my lips. It suddenly occurred to me that that was likely his first kiss since his divorce.
It was snowing so we didn’t linger as long as we both wanted to. The next night I met a friend for drinks and when I checked my phone, I saw a message from David.
“Hi, I’m finishing up dinner with my dad – care to hang out with me for a short bit?”
I was exhausted and about to head home, but couldn’t bear the thought of this wonderful man thinking I wasn’t excited to see him. Besides, he was only in town for a few more days. I told him to come over to the bar. David chatted easily with my friend, foreshadowing the next two weeks where he’d seamlessly immerse himself in my world.
And it’s a pretty great world.
We shared another chaste kiss in the snowy parking lot and David joked,
“Hopefully the weather improves so we can make out.”
The next night we played trivia with a few friends, one of my favorite hobbies. The brewery was crowded and there weren’t enough bar stools, so he stood behind me the whole night, reaching his hands through my overalls and around my waist. Instead of feeling self-conscious that a handsome man was touching my stomach, I leaned into his chest.
Overall, it was a great night. (And we won trivia.)
“Do you want to come inside?” I asked him when we got back to my apartment.
“Do you want me to?” he replied.
“Yes,” I said without hesitation.
We chatted for a while on the couch before kissing.
“I really can’t figure out what you want,” he said, pulling away.
“What do you mean?” I giggled in reply.
“I’m like, does she want me to kiss her, not want me to kiss her? I can’t figure you out. But I keep coming back for more.”
I giggled again.
“You have a wall up,” he said, intensely holding my gaze. “Why?”
Tears sprung to my eyes.
“I’ve really been through the wringer.”
He placed a palm over my heart and rubbed my chest soothingly. No one had ever done that and I was moved beyond words. We talked for a long time until he said,
“Do you feel that? Your wall is starting to come down.”
As we made out, he often paused to stare at me intensely and I tried not to shy away from this person who was so disconcertingly vulnerable. We talked and kissed for hours before he went home, and the next morning, he texted,
“I’m at a coffee shop with vegan breakfast options. Can I bring you something?”
Normally a text like that would have me internally screaming, “Ack! No! It’s the morning and I’m gross!” Instead, I found myself replying,
“I would love that, actually.”
We spent the better part of every day together after that, each day me asking,
“So, when do you have to get back [to your midwest home]?” He had originally intended to leave shortly after Christmas.
“I don’t know yet,” he would reply, eventually confessing, “I can’t seem to leave you, even though I’m making things more difficult for myself [with work and the house by delaying my return].”
We jokingly (but not) talked about him buying property in Bend after I learned that he didn’t actually split his time between Bend and the midwest. I also learned that he was still dealing with messy divorce paperwork, so “no ex wife” was an apt descriptor after all. But it was too late; I was already in too deep.
“I’m falling for you,” I said on New Year’s Eve, my voice wobbling.
“I don’t want to hurt you. I’m not ready for a full-blown relationship right now,” he said, tears in his eyes. “But I guess I already have hurt you.”
“I told you on our first date I was looking for a partner!”
“I know,” he replied. “I guess I’ve been selfish. I just haven’t been able to stay away from you. I wasn’t expecting this.”
“I’m solid in what I want; I’ve been at this dating game for ten years [since my own divorce]. I want this to be real, not just some summer camp fling. I’m scared this is just an escape for you, but this is my real life. I let you into my whole world.”
I introduced you to my Bend family!
“How can you say this isn’t real?” he said, tears landing on his cheeks.
On his last night in Bend, I cried for hours.
“I don’t plan on seeing other people,” he said, “But probably for different reasons than you. I need to focus on healing.”
We agreed we’d continue to talk and video chat and not see other people without telling the other first.
When he left, his text messages slowed and his phone calls were non-existent. A sinking feeling took over, punctured by random moments of hope when he’d text things like,
“Want to meet me in Mexico for my birthday? I’ll buy your ticket.”
“Well there’s only one answer to that question!”
Even though we made a couple of plans to see each other, he never followed through and I eventually confronted him via text. He immediately called.
“I’m completely humiliated,” I cried into the phone. “I bought bathing suits for Mexico! My friends keep asking about you! I’ve been solid and honest with you about how I’ve felt and what I want. You put all of this effort into ‘breaking down my wall’ and then look how you’ve treated me!”
“I know. I know. You’re right. About everything. I’m so sorry, Jules,” he said with his usual unguarded sincerity. “I got back home and everything just hit me and I chose to just not do anything, which was the shitty thing to do. But I wouldn’t be on the phone with you right now if I didn’t care about you. I didn’t expect to go on my first date in 13 years and connect with someone like this.”
Two hours later, we were back to flirting.
“I got my hair done today and I didn’t even send you a selfie,” I teased.
“Send it now.”
I did and he made a suggestive comment, prompting me to laugh.
“I like picturing you doing that little giggle of yours,” he said in response to a laugh I only seemed to do around him.
We joked some more and got even flirtier.
“Well, at least we know we always have that part,” David said. I, for one, knew I’d never been so attracted to someone -physically, spiritually, emotionally- in my life.
After that phone call, I was sure we’d stay in regular contact, but once again his texts disappeared. Completely defeated, I finally texted him that I would “let him off the hook” and start seeing other people. We agreed to have another video chat.
“Based on how things have been,” I began, “I’m just going to carry on with my life and not expect anything from you. No texts, nothing.”
“What are you trying to say?” he replied, seeming offended.
“I want to be in touch and stay connected, and we could use this time to get to know each other better, but that doesn’t seem to be what’s actually happening.”
“I selfishly want to stay friends so that maybe in the future I’ll still have a shot with you,” he confided. “But I know you don’t trust me anymore so that probably won’t work.”
Throughout the long chat, he said sweet things about all of the time we’d spent together.
“The day we went to the nacho place was one of my favorite times. That was a perfect day. I remember sitting there at the bar waiting for you and feeling so proud that I got to be with you and like I was the luckiest guy in the room.”
I reminisced with him, wondering if, one day, we might get back to that perfect place. I wished we could be there now. Instead, he knew I had to end our chat to go on another date. I couldn’t wait around for months, or even years, hoping he’d one day be ready for what we seemed to so clearly have.
“Well… I’d better get going…,” I said after we’d talked for two hours.
His face crumpled and he began to cry.
“I’m sorry,” he said. “That just really hit me. I wasn’t expecting that [to hit me so hard]. I’m sorry.”
We said goodbye and the only text I got from him came days later, asking if I’d gotten the sweatshirt he’d mailed to me weeks earlier (one of his that I loved and he’d wanted to surprise me with). I said it hadn’t arrived and heard nothing from him after that.
“Just think of all he’s going through,” a close friend said when we did a deep dive into the situation. It had been well over a month since our last exchange. “He’s dealing with all of the ex settlement shit. He’d have to tell his family and friends he started dating the first woman he met – online. He has a therapist telling him not to get into another relationship right now. He knows you’re dating. And you didn’t text him on his birthday. He probably thinks you’re mad, that your friends hate him, that YOU don’t want to hear from HIM. Maybe he thinks you got the sweatshirt and never said anything. I think you should reach out and tell him you’re not mad, just sad, and hope he’s healing.”
I took a deep breath. I’d already given her my rock solid counterargument of, ‘Or he’s over it, never felt what I felt, and I’ll look even more pathetic.’
Two days later, I bit the bullet and took her advice.
“Welp, the sweatshirt never came,” I texted, “but I promise I wouldn’t have burned it [like we joked about]. 😆 I was sad to not text on Valentine’s Day and your birthday, but I wasn’t sure what the right thing to do was. I feel like it’s important to say I’m not mad, just sad, and I hope you’re healing. ❤️”
I hit send and tried to come to peace with the idea that he might never reply. A little over five hours later, he did.
“Hi, thanks for texting it’s good to hear from you and I appreciate you saying that ❤️. I’m sorry I never resent [the sweatshirt], it just felt weird to me given our talk. It was a tough birthday this year but I think I’m doing ok. I hope you (and uncle Jesse) are doing well out there.”
I burst into tears which turned into sobs. His response felt so…distant.
…So I guess I’ll be buying my own sweatshirt.
I waited an hour and a half before deciding I needed to say more. What did I have to lose?
“I’d left the door open based on our last video chat,” I wrote, “especially in terms of keeping in touch (which is where I thought we’d landed), but have been interpreting the [six weeks of] radio silence to mean you’d prefer to not be in each other’s lives… Either way, the earlier sentiment stands and I’ll be thinking about you. ❤️”
He replied two days later with a typo-riddled message.
“Hi Jules, I know we did. I’m sorry I am not in a place to do that and I’m sorry that you are sad 😞. I appreciate that you are understanding of me and what I have going on.
“For what it’s worth I also want to say this because you should know it: I think you are an amazing person. You are super funny, I haven’t laughed as much in a long time. you are kind and thoughtful, I still feel so thankful that you put together all that food for my road trip. I appreciate you let [sic] me hang out with you [sic] friends who are all so welcoming, thoughtless [sic] and awesome people in general. I throughly [sic] enjoyed just talking with you and all our great conversations. I think you have great morales [sic] and love how you stick to them while also being understand [sic] and compassionate to others. You are also very pretty and I appreciate how you take care of yourself and Uncle Jesse ❤️”
I read his message twice, surprised when only a single tear fell. After another moment, I clicked ‘Archive,’ and after a few moments more, started to feel my heart lighten.
~*~*~*~*~
It’s tempting to give up, but with each heartbreak (this one arguably the worst since my divorce in 2014), I’ve started to better understand how our capacity to love expands indefinitely. Just as when we welcome a new child or pet into our lives, we don’t trade old love so we can afford to love this new being.
I know now that I don’t need to “get over” this love. I just need to make room for new love.
“So should we meet to grab a drink sometime this week?”
I’d lost track of the number of times I’d typed that phrase into the Hinge or Bumble chat box. Usually after a day or two of chatting, but sometimes after a multi-week, back-and-forth investment.
I wasn’t sure if it was my age (40), some sort of collective post-COVID social anxiety, or pure laziness, but suddenly the mental load of dating seemed to fall squarely on my weary, stress induced rash-covered shoulders.
“What is this?!” I cried to girlfriends during trivia last week, shoving my phone under their noses.
What are you up to this week? -Rich
How’s your week been? -Tom
How was trivia? -Ben
“All of them! All of them are doing this! And with these dudes, we’ve ALREADY BEEN OUT. And now they won’t stop texting! But they won’t ask for another date! I DON’T HAVE TIME FOR THIS.”
“Did you meet them on Bumble?” one friend asked. “I have this theory that maybe it’s training men not to make any moves [since Bumble requires that the woman ‘make the first move’].”
“Some were Hinge,” I replied. “But you might have a point. I think I did initiate the first date in all cases. …Are they just not that into it? Back burner-ing? Friend zoning? Too scared to wind up on my blog?”
There had been an impressive uptick in Dates Who’d Discovered My Blog Before Meeting, after all.
Hi boys. Told you I always change names.
I sighed and put my phone back in my purse, trying not to think about the last three dates I’d line up – all canceled, by them, just hours before our meeting time. A bone deep weariness and latent anger threatened to take over as I recalled all of the recent dating disappointments – including one crushing heartbreak.
“Don’t worry. I understand women. Like I knew you took your purse to the bathroom just now because you have your period.”
Gross.
“You’re having so many bad dates because you need to improve your screening process.”
F&@% you.
“If you did run a background check on me, you’ll see that I have a restraining order out against me by my third ex-wife for strangulation. But it’s not true.”
Help.
“I’m just not ready for a relationship.” x 1,427
You don’t say.
Not just the mental load of making plans, carrying the conversation, and offering to pay (all still resulting in little more than the above), dating was taking its toll in deeper, identity-challenging ways. Had I lost my ability to read the room? Could I no longer tell the difference between sincerity and narcissism? Genuine interest and politeness?
Meet Cary, a first date from a month ago.
“Hey! I just got done with a long training run and I’m STARVING,” I typed into Hinge. “Any chance you’d be up for meeting at [x] or [y] restaurant instead of the whiskey bar? [Y] restaurant has a full bar! And I promise I’m not trying to score a free meal – I’ll even share!”
I pressed send on my message to Cary, feeling bold but a little bad about proposing a last minute change. Twelve years my senior and brimming with goofy photos and energy, I assumed he’d reply along the lines of, ‘I got upgraded from first date drinks to dinner on a Saturday night?! Score!’
“Y restaurant is fine,” he responded 15 minutes later. I gulped.
“I can try to eat quickly here and keep the original plan,” I backpedaled, a knot forming in my stomach. Was he really that stuck on the whiskey bar? Should I have kept my mouth shut since girls are supposed to be pretty and agreeable and never hungry?
“No, your happiness is important. And I’m easy.”
The knot grew and I shook my head. Certainly I was reading into what seemed to be “off” replies. Besides, I didn’t have time to worry about it if I wanted to finish drying my hair and keep our original meet-up time. I put on a fitted shirt, corduroy skirt and winter tights, leaving my hair down. I raced to the restaurant to make sure I could get a table for us and not cause any more drama with the change in plan.
Feed me.
A minute or two after 5:30, Cary walked in, unsmiling. The knot in my stomach became a full on Boy Scout lesson.
I’ve definitely earned the badge for this one. Photo by Will O on Unsplash
I sprung up and opened with my usual,
“Hi! Are you a hugger?”
Cary was much slighter than I had imagined and we hugged awkwardly.
“Are YOU a hugger?” he replied after we were already embracing, a tone to his voice that might have been teasing if not for the edge. I laughed nervously, failing to think of a witty comeback.
“Thanks so much for your flexibility with the change in plan,” I blurted as we sat down.
“Do you normally have trouble asserting your needs?” Cary retorted.
“Well it depends… In dating situations, usually not…,” I started rambling. “Not with my family, especially not my sister. But with friends…” Could he tell how flustered I was? “Anyway thanks again so much for your flexibility! I’m so excited to eat! Have you been here?”
“Yeah, I actually live nearby,” Cary said, still not offering any smiles, a stark contrast to the silly poses in all of his Hinge photos.
Okay, so the location change shouldn’t have upset him… What was the problem??
“I guess I should order if you’re eating,” he continued, looking at the menu.
“Oh, you don’t have to! I’ll shamelessly shove food in my face by myself,” I joked to no effect.
“Do you care if I get beef tacos?” he asked, knowing I was vegan.
“If I cared about things like that, I’d be upset a lot,” I teased, still trying to lighten the mood.
“Okay, I’ll get fish.”
I stared at him.
“I was kidding,” he replied, and proceeded to order the meat tacos. And beer, despite me reminding him that they had a full bar and he could get the whiskey drink he so obviously had had his heart set on.
We carried on the kind of painful conversation you might have with a distant, visiting relative; plenty of questions asked, but only out of pure obligation. I couldn’t for the life of me pinpoint the issue, but I felt like the nerdy high schooler whose older cousin was forced to take her to prom.
When the waitress brought the check an hour and a half later, I quickly grabbed it.
“Ah-ah, this was my idea. I’ve got this.”
“We can split it,” Cary offered half-heartedly and I fought the urge to roll my eyes.
“Excuse me, I have to use the restroom,” he continued.
I grabbed the bill and ran it up to the counter, desperate to get out of there as quickly as possible. Cary didn’t walk me to my car, instead giving me another awkward hug outside.
“Nice meeting you,” he said and took off in the opposite direction like he had somewhere much better to be.
The whiskey bar, presumably.
I got in my car and stared at the clock. 7:15pm. 7:15pm on a Saturday night and I was alone. Thirty minutes later, I got an alert that Cary had messaged me through Hinge.
“Thank you so much for dinner. You are really sweet and kind. I don’t think we’d be a great fit romantically. [sad face emoji] And I want you to find your guy and get off the apps! It was fun chatting tonight and I enjoyed your company.”
No. He. Did. Not. I stared at my phone in disbelief. Pour a little salt in the wound much?! I gathered myself before uncharacteristically responding (given that my go-to move is silence).
“Haha yeah… I read the room and you immediately gave the distinct impression that you did not want to be in said room. No worries! Take care!”
I put my phone down, poured a manhattan, and fired up Emily in Paris – a mental load-free plan that never disappointed.
I clicked on the Hinge dating app message. It was always nice to see some text on the screen instead of a lazy ‘like’ with no accompanying message.
In case you’re wondering what zero effort looks like.
Greg’s profile photo was slightly menacing -dark beard, unsmiling, his face filling the entire frame- but I was intrigued by his comment on my voice prompt. (Hinge allows us hopeless romantics gluttons for punishment to add video and voice memos to our profiles.) I quickly scrolled his profile and saw that he ticked all of my major boxes: non-smoker, vaxxed, liberal, didn’t appear to live in a van. He had also included a voice prompt and when I clicked on it, I heard him say, “You can tell a lot by a person’s voice. In fact, 90% of your connection to someone is through their voice.”
“So does this mean I’m already 90% golden and I can coast from here?” I replied.
Witty banter immediately ensued.
“Oh wait, you like to meet up,” Greg wrote after a couple of back-and-forth messages.
Translation: Let’s just get this over with.
I decided to shuffle a few plans that evening so I could reply, “Yes! The snag is that I’m only free tonight or after next Monday.”
“I could meet tonight at 7:30,” he immediately responded, offering up a couple of locations.
We solidified the plan and exchanged a few more funny messages throughout the day. When I walked into the bar just after 7:30, I felt flushed from the bitter cold central Oregon air, my hands shoved deeply into my trusty brown puffy jacket.
That coat is even older than this blog! Photo: Jan 2014, Freeport, Maine.
I immediately spotted Greg at a large table and he greeted me with a prolonged handshake and big smile. He looked like a stand-up guy with his act together and I inwardly unclenched. He was a bundle of nerves, but in a charming way – the kind of person who has a million things to say when they’re excited.
A welcome relief when half of my first dates look like this.
Before we got too far into our frenetic conversation, Greg popped up.
“I ordered at the bar, but let me make sure someone is coming over to the table.”
Point one for Greg, I noted. My most recent first date had been sitting with a drink when I’d arrived and didn’t offer to get me anything, which always gives me pause.
“So you’re a writer?” Greg asked after confirming we had a waitress.
Greg offered up lots of questions and though I never quite got to finish any train of thought before he bounced to something else, I was flattered by his interest.
“I’m a lightweight,” he said when ordering his second hot toddy. “I usually only have two drinks.”
“I’m German and Irish. And I don’t have kids [like you]. Don’t try to keep up with me,” I teased.
I could tell he was feeling a little loose about an hour into the date and I wondered if things would get sloppy.
“Do you have any celebrity stories?” he asked and we both launched into our best tales.
“I usually don’t tell the story like this,” he said while I was on the edge of my seat. “You must bring out the writer in me!” He had built his story so that I was left guessing the celebrity the entire time. I loved it.
Throughout the night he dropped dozens of compliments and I wondered if there could be any romantic spark. I knew I liked him a lot and could definitely see us having fun as friends.
Two hours into the date, I got up to use the bathroom and when I came back, I noticed how buzzed Greg was and knew I was ready to go home.
“It’s so freezing in here,” I said and we both pulled on our jackets.
“We could go have another drink back at my place,” Greg offered with a grin.
My heart sank and emotion took the wheel.
“Noooo, Greg,” I moaned.
“It’s totally innocent! We live in the same neighborhood!” he said, still smiling, trying to warm me back up. “Damn. I can see you’ve put up a wall now.”
“This keeps happening!” I explained, only partially teasing. “Every first date, guys keep asking me to come home with them. It’s not cool.”
He continued back pedaling and I continued spiraling, not having the energy to recover gracefully and smooth things over. I just wanted to go home. I was exhausted from the endless dating rollercoaster: the adrenaline rush of meeting a perfect stranger, the ensuing trickles of hope, nightmares, occasional magic and inevitable let down.
I’m so glad I put on Spanx for this.
“I was married for 20 years; I understand women,” Greg said in a last ditch effort to win me over. “Like I know you took your purse to the bathroom because you have your period.”
I blinked. After a long beat, I blurted,
“I’m really uncomfortable and I’m gonna go.”
“…Okay,” I heard Greg reply, flabbergasted, as he watched me bolt into the frigid night.
As soon as the cold air hit my cheeks, I felt a flood of relief. …Immediately followed by shame and regret. Did I just completely overreact? Am I going to be “the crazy blonde” he tells his friends about? Should I apologize? This was a small town and we were practically neighbors, after all.
I suddenly realized I had ten minutes to make it to the grocery store before they closed, securing the much-needed lemon I’d forgotten earlier that day.
By the time I got home and opened Hinge to apologize, Greg had unmatched me. When you’re unmatched, you lose all access to your chat history and their profile. The ultimate slap in the face in the online dating world. He had sent his number in the Hinge chat right before we met, but I didn’t save it.
Well f*%&.
So, “Greg.” If you’re out there, I’m sorry I didn’t handle that more elegantly. My bad. But maybe stick to two hot toddies next time.
My opening line to Kevin on Hinge paid tribute to his profile prompt: “Dating me is like…finding that $5 bill in your jacket from last season.”
I wasn’t sure if I should message him. At 31, he was nine years my junior and his profile featured a series of photos that each looked like a slightly different person. Long hair, short hair. Beard, no beard. Muscular, pudgy. But there was one photo I found irresistible: He was hitchhiking, thumb out, wide smile, holding a sign that read, “Late 4 Summah Skool.” I’d later learn that the photo wasn’t staged and he had in fact had great success hitchhiking all over the country – as long as he held a funny sign.
Even though I’d long sworn off marathon messaging on dating apps (“Let’s skip all the messaging and meet up to see if there’s a genuine connection,” my profile currently reads), we quickly fell headfirst into the kind of dazzling banter I liked to imagine Aaron Sorkin spotting. (“Holy shirtballs, Jules, I’ve been waiting decades to find a writer like you!”)
“My entire being is concentrated on not making typos because I’m a writer and we have a reputation to uphold,” I wrote that night after several glasses of wine.
“My entire being is concentrated on not making typos in fear that a writer will *eviscerate* me,” Kevin replied. “Yes, allow me to flex my associates degree in spelling.”
“If someone ever gave me a degree for spelling, I would propose.”
The teasing went on for hours and I lost track of the amount of times I laughed out loud. He reminded me of my ex-husband’s most attractive qualities. Witty. Masculine. Confident.
“I just want someone who sparkles – like my friends do!” I’d been telling girlfriends over the past few months. After several years of dating off and on in central Oregon, it seemed like I was asking for the moon. “The kind of guy who’s really comfortable in his own skin and treats you like you’re the hottest thing he’s ever seen and knows he’s THE MAN because he gets to be with you.”
Messaging Kevin on Hinge, I began to wonder if he just might fit the bill.
The $5 $20 bill.
Two days later, we made plans to meet at a dive bar at 4pm, a couple of hours before my friend’s holiday party. Kevin showed up early and secured a booth, his funny messages continuing right up until the moment I walked through the door. My heart pounded. I wondered if, instead of carrying the conversation like I often did on first dates, I might actually have trouble keeping up with this guy.
I spotted him immediately, wearing a worn-out, turquoise shirt and baseball cap. He was slightly taller than me and just as masculine as I had imagined, right down to the beard and rock solid hug.
I sat down and when he smiled, his eyes glowed and my stomach somersaulted. Everything in my body told me that this was going to be a good date. Really good. He stared at me silently for a long moment until I finally said,
“What is it…?”
He grinned and then, in his deep and gravelly voice, said slowly, “You’re a fucking smoke show, Jules.”
I laughed and he reached into his pocket. “I’ve got somethin’ for ya.”
He pulled out a small slip of paper and as soon as I saw it I said, “Well, I guess I have to get down on one knee now.”
“So should we just get all of our red flags out now?” he asked.
“Tit for tat? Let’s do it,” I answered, palms flat on the table, accepting the challenge readily.
“I have no money,” he began and I giggled.
He went on to explain that he was newly single, had a crappy-paying but steady job, and would be traveling for work for six months, starting in April.
“Well if we hit it off, you’ll just have to get a new job,” I said, unfazed. His red flags were no match for our instant chemistry and what I quickly learned was an identical life philosophy.
“I always make decisions based on what will make the best story,” he told me.
You don’t say, Kevin.
“Do you want to come to this holiday party?” I found myself blurting as the clock neared 6pm. “It would make a good story.”
“Do you want me to?”
“It’s going to be a grown-up-y cocktail kind of party,” I cautioned.
“Do you want me to come?” he repeated.
“Do you want to go?” I asked.
“Yes or no, Jules.”
The way he leveled me made my heart flutter. Of course there was only one answer.
“Yes.”
We spent nearly the entire party canoodling on the living room couch and ignoring everyone else. Resting a hand between my crossed legs, he confessed that he was dealing with not only a bad break-up, but a tragic family death, his eyes welling with tears.
“We don’t have to talk about this now,” I said gently, my hand on his knee.
“It’s okay,” he said. Later, he would say that he didn’t really talk to anyone -besides his new therapist- about this.
“Can I kiss you?” he asked at the end of the night, long after the party had ended and after another drink back at the dive bar.
Just like the last question he’d asked, the answer was crystal clear.
When I got home around midnight, we texted for hours.
“You’re going to have to give me a minute to believe all of this is real,” I confessed via text. “You just started dating again, but I’ve been at this for years.”
“Tell me how I can help.”
“Just keep touching my butt and complimenting me.”
We hung out again the next night with one of his friends at yet another dive bar.
“I missed you. I’ve been telling my friends about you,” he whispered after I sat down next to him.
When his friend left for the night, he gave us a little smile and thumbs up, clearly approving our undeniable connection.
“I’m all in,” Kevin blurted once it was just the two of us. “But that’s a conversation for another day.”
We were both too exhausted to hang out again the next night, Sunday, and doubt started to creep in when his messages abruptly slowed. Had he changed his mind? Was this real? Were we really a match? Was it moving too quickly? Was I being love bombed?
“Brad and I spent every day together when we first met,” my friend, Amanda, reassured me. “We moved in a few months later and now we’ve been together 17 years!” She was on Team Kevin, or rather, Team Jules Needs a Goddamn Break, and had met Kevin at the holiday party.
Despite the sudden halt in messaging and a couple of short, lackluster phone calls, Kevin came over on Monday night and I greeted him with a kiss, trying to overcome my insecurity. Later, when he asked if I wanted him to sleep over, I said,
“I think we’d need to talk about what that means.”
“I’m the lowest I’ve ever been,” he confided, our limbs intertwined on the couch and my dog nervously panting, wondering who this strange man was. “I do ultimately want a partner, and I think I’m ready for that. I don’t know. One minute I feel one way, the next minute another way. I’m kind of all over the place. I really like you and want to keep hanging out. I can’t promise I won’t go on other dates; I’ve just put myself back out there, but I think you’re great. You’re a catch, Jules. …Does that help?”
Part of me felt relieved by his monologue. It was more tempered and realistic. After all, I was still planning other dates myself – we’d only known each other for four days.
We made out until the wee hours, the chemistry overwhelming. When he left at 2am, though, I was suddenly crying. I knew something was off. The next morning, I Googled “dating a grieving man” and read for two hours. It seemed to explain the hot-and-cold behavior, but I still felt unnerved. His actions were the same kind you see when a guy, well, just isn’t that into you.
“It’s so confusing. I really like him and I haven’t felt chemistry like this in so long,” I sighed, twirling the straw in my vodka tonic, chatting over drinks with a friend.
“Just go with your gut,” she replied. I wanted to feel comforted, but I genuinely wasn’t sure what my gut was telling me.
After distancing himself even more for two days, Kevin asked me to call him that Thursday night, which I did. He didn’t pick up. The next day around noon, my phone rang.
“What’s shakin’ bacon?” he asked in his gruff voice, despite me teasing him that that was a pretty bad nickname for a vegan.
“What’s cookin’ good-lookin’?” I replied, feeling fairly confident that he was going to lockdown some weekend plans and that I was better equipped to navigate his grieving behavior.
“Nothin’ much, just watering plants.”
“Making plans?” I questioned, mishearing him. “That makes my project manager heart flutter.”
“Watering plants,” he repeated.
“Ah.”
“What are you up to today?”
“Just getting some work done, then exercising. That’s about it for today,” I answered, my pride not allowing me to initiate any plans. “How about you?”
“Nothin’ much. I got volun-told to bring fish for sushi-making tonight, so I gotta get that together.”
My stomach sank. On our first date, he’d tried to woo me with the promise of a dinner date at his place, making avocado and tofu sushi. “I almost never eat meat,” he had said – music to my ears. Now he was talking about bringing sushi somewhere else? Somewhere I wasn’t invited? Somewhere with another woman…?
“My red flag is my massive jealous streak,” I had told Kevin on our first date. Even though I called it my red flag, I knew a sensitive, loving partner would do everything in his power to make me feel secure. I was beginning to realize what my gut was telling me. Run.
“And you have your work holiday party on Saturday,” I added, trying to play it cool. Would he invite me to that?
“Yeah, I really don’t want to go, but I got talked into it. They want us to dress up, but they don’t pay me enough for that.”
We chatted about his notoriously raucous holiday work party for a minute and then he said,
“So…I need to talk to you about something.”
A pit formed in my stomach and I braced myself, trying to go numb.
“I’ve been thinking about it a lot,” he continued. “And I really don’t think I’m ready for a relationship. I’m leaving [for work] in April and it would just be a waste of time. I know that’s what you’re looking for, and I’ve been trying to figure things out, and I wanted to be upfront.”
“Okay. …Thanks for being upfront,” I said flatly. A waste of time?
“I’d still like to hang out, though. I really like you. But of course that’s up to you.”
I let that hang in the air for a moment before saying quietly, “I think that would be confusing.”
“Okay,” he seemed almost surprised, and maybe disappointed, by my answer. “I hope I didn’t ruin your day.”
Fire flared in my chest. How. Dare. You. I swallowed thickly, willing myself not to cry. I thanked the heavens for instilling me with enough self-worth and stubbornness to recognize this situation for the utter bullshirt that it was – even if my heart was cracking in a few dozen places.
“No,” I said firmly, my mind racing to plot out the rest of the day. 1. Cry. 2. Finish work. 3. Make plans with sparkly friends. You do not have the power to ruin my day, you motherforker.
“I’ll leave the ball in your court. If you decide to text me at any point, it won’t be weird. I would like to hang out. But like I said, I’ll leave the ball in your court.”
“I guess we made a plan after all,” I deadpanned. “…Bye.”
I archived our text message thread, wiped away a few tears, and grabbed my laptop. Better things were waiting for me.
Justin Timberlake? Did you hear that?
~*~*~*~*~*~
P.S. – I know, I know! I never gave you an update on Mr. Brought Roses to Our First Date. We had a few more very nice dates, he accidentally gave me COVID despite having never touched me, and we’re now friends. I think. I obviously have no idea what I’m doing.
I twisted the last strand of hair around my curling iron, staring into the bathroom mirror. Every time I did my hair, I felt like a teenage boy trying to unclasp a bra.
Okay.Not bad.
“Bing!” my phone sounded. I walked the short distance through my bedroom into the living room to check it.
“Hey! I’m so sorry. My roommate is in the hospital.”
Dennis, my 20-something Hinge (first) date for that evening, had just thrown me a curveball.
“Oh no! Are they okay?”
“Yeah, everything is fine. But I’m afraid I won’t make it tonight. I hope you’ll let me make it up to you.”
I chewed the inside of my lip. On the one hand, I wanted to sound supportive. On the other hand… I snapped a selfie and sent it.
“I’m so glad they’re okay! But you’re buying the beers next time because I did my hair and everything.”
“Aw man, you look so pretty. And absolutely.”
A few days later, we made plans to meet at a local food truck lot for happy hour. Once again, I stood in the bathroom curling my hair – one of my least favorite activities, but one that turned my fine, straight hair into something a bit more alluring.
Or so I continue to tell myself.
As I got ready to leave, my phone chirped. I looked at the screen and saw a text from Dennis.
“Hey, just got home. Don’t think I’m gonna make it tonight.”
My mouth sagged and tears pricked my eyes.
“Why?” I wrote back after a moment’s hesitation.
“Just not feeling it.”
My stomach fell along with a tear. My mind raced with a thousand things I wanted to say and continued to do so for the next 24 hours. Instead, I decided to say nothing.
“I’m really sorry about last night,” Dennis texted the following morning. I never wrote back.
“Of all my worst dating stories,” I recently told Henry, central Oregon’s last remaining gentleman, “the absolute worst was this guy, about a year ago, who basically stood me up – TWICE. The second time because he ‘just wasn’t feeling it.'”
“You’re kidding,” Henry replied in shock.
“I think it was social anxiety, but still. It REALLY hurt my feelings.”
This week, I received a new Hinge like. It was Dennis. A year after he’d stood me up. I finally seized the opportunity to say what I hadn’t said before.
Maybe I was wrong to lecture him, but I wanted to shake him out of his own self-centeredness. How many times had I rallied to meet a friend or first date so I wouldn’t hurt their feelings? Seeing Dennis on Hinge reminded me of a similar dating story earlier this year with “Craig Who Cancels,” one of the strangest dates I’ve ever had (and you know that’s saying something)…
“I’m actually a stand-up comedian,” Craig explained as we messaged back and forth via Bumble.
“No way!” I replied, gearing up to geek out on our favorite stand-up comics. After a few more messages, I invited him to meet me for Friday happy hour. “I’m going with some girlfriends, but it sounds like you can hold you own.”
“I love working a crowd,” Craig fired back, agreeing to meet me at the brewery at 4pm on Friday.
Around 2pm on Friday, I received a bizarre message:
My girlfriends and I attempted to decipher the confounding note.
“Maybe he has Covid and doesn’t want to say.”
“Maybe he panicked.”
“Maybe he started seeing someone else.”
Disappointed, I wrote Craig off and turned my focus to other activities and matches. A week later, and despite having my phone number, I received a new message from Craig on Bumble saying he had two extra tickets to a comedy show. It wasn’t clear whether he was offering both tickets to me or fishing for a date.
While waiting to see if my friend was available to join us, I switched our conversation back over to text messaging. Which is when things got even more interesting:
When I got to the comedy club, Craig greeted me with a hug. He was more nervous than any date I’d ever met, his voice trembling.
“Whew, I’m really blowing it,” he said, stumbling over the bartender’s name while trying to place our drink order.
Turns out the nerves were date-specific and he was a regular performer at the comedy club. He began introducing me to everyone in the small venue and I sunk inside my cold shoulder sweater.
Because I knew three of them.
Because I’d gone on first dates with them.
Apparently I have a type.
“Congratulations on a [recent promotion I saw on a Facebook group we have in common],” I said to Marty, an older guy I’d gone on a walking date with several months earlier (who then ghosted me after I turned down his second-date-booty-call proposition).
“Oh thanks,” he grinned, his overconfidence nearly balancing out Craig’s nervousness. “We went on a date in…December, right?”
My eyes darted over to Craig, whose expression I couldn’t read. “That sounds about right.”
Marty looked at Craig and raised his eyebrows.
“As I recall, I didn’t make it to a second date.”
I raised my eyebrows in return.
“That is correct.”
Unfazed, Marty chatted with Craig for another moment before flitting off to someone else; he was the MC for the night and clearly enjoying his role. For a small local comedy club, the show was surprisingly tolerable. Funny, even.
“I’ll call you,” Craig promised after walking me to my car at the end of the night.
“Has anyone ever brought me a gift or flowers on a first date?” I wondered, driving slowly through quaint downtown Bend, Oregon, careful to dodge the pedestrians who often crossed the street willy-nilly. “Do people even do that anymore?”
Making a mental note to survey my girlfriends, my mind drifted to the previous night’s date…
***
“Hi Paul!” I greeted with a wide grin.
Paul was ten minutes late, a bootleg version of his Hinge profile photos, and unsmiling.
“Hey,” he replied, not making eye contact.
We sat at a picnic table in one of my favorite food truck lots and, sensing imminent disaster, I blurted, “Should we get a drink?”
“Okay,” he agreed, his face unreadable.
“Have you been here before?” I questioned while Paul stared at the beer menu.
“Yeah,” he deadpanned. “Like a year ago.”
“I’m gonna grab something from the cooler,” I said, walking away to procure a can a.k.a. half bottle of sparkling wine, which apparently I was going to need to shotgun in order to survive the next hour.
When we sat back down, I immediately took charge of the First Date Starter Kit questions: work, hobbies, family. With each query, I got a one line reply with zero return questioning.
Twenty minutes in, I decided to see what would happen if I stopped talking. Paul stared at the ceiling.
“So do you live with roommates, or…?” I casually began again. I’d learned that that was the most tactful way to ask about a first date’s living situation. Especially one in his 20s. (Hey. I’m open-minded.)
“I moved back in with my parents to save money,” he replied and I kept my expression neutral.
Oh, Paul. That’s wonderful.
“Smart,” I answered. “Houses are so expensive here.” I paused. “I saw on your profile you like Harry Potter. I LOVE Harry Potter. I saw Harry Potter and the Cursed Child on Broadway last December and it was the best show I’ve ever seen!”
“I’ll have to check it out,” he replied in monotone.
‘Check it out’? In central Oregon? Does he not understand where Broadway is?
After ten more minutes, I surrendered and pulled out the Ace I’d tucked in my back pocket: A subject I had no interest in, but suspected would light him up.
“So tell me more about motocross! Is it moto-cross, without an ‘r’ in the middle?”
“Yeah, mo-to-cross,” he replied. I couldn’t tell if any enthusiasm was building.
“That trips up my brain! Tell me everything; I know nothing about it.”
“Well,” he began, shifting in his seat and staring over my left shoulder. “It’s on a closed course, and…well. Um. Yeah. I don’t know. I guess it’s hard to explain.”
“Allllll right everybody!” a booming voice announced from the back of the room. “Trivia is just about to begin so make sure you submit your team name!”
“Yikes,” I grimaced at the volume, but then immediately sensed a golden opportunity. “Gosh, I think it’s going to be too loud to talk now. I’m sorry I had no idea they had trivia here! You finished your beer so we should probably call it, huh?”
Paul moved his head in a way that was neither a nod nor a shake. I stood up, chugging my wine. I didn’t even care that I’d have to sacrifice more than half the can by leaving 25 minutes into the date.
As we walked outside, I quickly turned the opposite direction while calling out, “Thanks for coming out tonight!” I made a beeline for my car, relieved he didn’t suggest we go anywhere else. I instantly dialed a friend’s number.
Tonight’s date, Henry, seemed to tick all of The Jules Boxes and then some: My age, liberal, vaccinated, didn’t want kids, active, smart, social, good job, lived alone, dog owner – and “98%” vegan. On the voice recording accompanying his profile (Hinge lets you add audio and video), he sounded gently masculine, thoughtful, and eloquent. In the few messages we’d exchanged, his responses had been fun and sincere. When I’d mentioned seeing local live music that week, he’d looked up the musician and then sent YouTube clips of other songs he’d thought I’d like based on my taste.
When I walked inside the wine bar, I was sure he’d already be there. Instead, he wound up being a few minutes late and a knot in my stomach began to form. Maybe I was wrong… Three minutes past our meeting time, I looked to my left and saw a well-dressed man walking towards me.
Carrying a bouquet of long-stemmed roses.
*mic drop*
“Hi Henry! Are you a hugger?” I said, walking towards him and going in for one.
“Hi Jules! I am!” he said, wrapping his arms around me. He was solid, and at 5’11”, a few inches taller than me. He didn’t even lie about his height!
“Thank you SO much!” I exclaimed, taking the roses and admiring them. I felt several sets of eyes on us as we walked back to our table. “They’re gorgeous!” I put them to my nose. “And they smell amazing!”
“There’s 11, because you said 11 was your favorite number,” Henry explained, taking his coat off and draping it over the back of his chair. I instantly noticed his shirt.
‘No one dresses like a grown-up here,’ I had lamented to friends a week earlier. ‘Like what ever happened to a nice button down shirt?’
Henry’s button down shirt was impeccably tailored, pressed, and tucked in; white, with tiny blue stripes. You could tell he worked out by the way it hugged his torso. My stomach started to flutter. Was I prepared for an actual date? With a fully adulting human male?
This was a first.
“So how’s your day going?” Henry asked.
The conversation flowed from there, though I occasionally tripped over my words.
“Oh no no, you go,” he said every time we spoke at the same time.
“I don’t understand why people would put up a misleading photo,” he said at one point, when the inevitable ‘online dating’ topic arose. “You look exactly like your photos.” He smiled, clearly giving his approval.
I definitely didn’t stress all day wondering what to wear and then put on the outfit I always do, Henry.
“I also don’t understand when people roll into a first date like they can barely bother to be there,” I replied. “I feel like you have to treat every first date like it’s special.”
“Because you never know!” we both said at the same time.
When the date ended a few hours later, Henry walked me to my car and gave a solid hug goodbye.
“I’d love to do this again sometime.”
“Me too!” I answered.
“Send me your number through the app, if that’s okay?”
“I will!”
Shortly after I’d gotten home, Henry’s first text arrived.
“Such a wonderful evening! I wish it would have gone longer!”
After a few more exchanges, he said, “I have to say this was an awesome first date. So, I’m pretty much free anytime to see you again so whatever date works for you, I’m totally available.”
Single men of the world? I hope you’re taking notes.
“We’re sorting zee last fruits of zee year today, and these, they go together at zee same time.”
“Uh-huh.”
The 6-foot-3 French Hemsworth swaggered towards us carrying two bunches of grapes, one white and one red, leisurely popping the small orbs into his mouth.
“It’s our last day of sorting today,” he repeated, casually spitting seeds off to the side.
“Uh-huh.”
The three of us stared at him, mouths agape, borderline catatonic. A flash of bright white blinded us when he smiled.
Erin, Babs (mom) and I had been finishing a winery tour in the Willamette Valley when we’d spotted two bald eagles flying overhead.
“Look!” Erin had exclaimed, catching the attention of a tall, brunette Adonis sorting grapes. He’d sauntered over.
“What do you think zey are looking for?” he had asked, his elegant neck craned skyward.
Upon hearing his French accent, Erin hadn’t wasted time in replying, “I think they spotted a tasty treat.”
“Do you agree?”
He had torn his gaze from the sky and laid a set of smoldering eyes on her.
Paint me like one of your French girls.
Babs and I had watched the scene unfold in a state of disbelief. Was this a real human? Did men like this exist outside of Hallmark holiday movies? Was he about to tell us he was inheriting the winery from his late uncle and the only thing missing was an awkward blonde to share it with?
“Here, try,” he said, offering us the two bunches of grapes cupped gently in his masculine palm.
After a six month dating hiatus following Cameron Who Cancels and Wasn’t Even Worth Blogging About, I evidently hit my head and decided to fire up Hinge. Again. Living in central Oregon -an island of sorts, surrounded on all sides by forest and desert-y nothingness- I knew I was bound to see some familiar faces. When a cute, new, outdoorsy guy sent a like, I cautiously accepted.
“Hey Jules, how’s your week going?” asked Walter.
Not exactly a panty-dropping opener, but I decided to reply. After a few brief and normal-seeming exchanges, we agreed to meet up the following week after he was done hosting his parents. He was about my age, liberal, had a good job, a dog, and a solid grasp on “you’re” versus “your.” He even picked our meet-up spot instead of punting the decision back to me. What more could a tired, 40-year-old divorcee ask for?
When our 7pm Thursday Date Night arrived, I put on a new cream-colored turtleneck sweater and light wash jeans, arriving a few minutes early.
Jules Schnedeker (b. 1982). Fruitless Effort, 2022. Google Pixel photo on blog.A self-portrait captured before the artist fell into another writer’s block.
Shortly after 7 o’clock, I caught a man waving at me from outside the restaurant. Walter came inside looking frazzled.
“Jules? Hi. I think I left my oven on.”
His eyes held a wild, frantic look.
“Oh no! Okay. Well, you should definitely go check.”
“Are you sure?”
“Of course! You don’t want to be worrying about that the whole night! I can go meet you nearby…wherever you live,” I offered, realizing I was about to reveal that I’d already stalked him online and knew his last name and a few other key details.
“Oh, but this place looks so nice,” he lamented, gazing around the restaurant.
“Why don’t I get us a table outside by the fire and you just come back after you check,” I suggested.
Walter looked relieved. “Okay, I live about 10 minutes away. Thank you so much.”
“No problem!”
I sat down outside, eager to get a glass of wine. As the minutes ticked by, I started to wonder if I’d just been ditched. Nah. He wouldn’t have bothered to come inside if he was gonna bail. A half an hour later, Walter finally returned. The moment his rear end hit the chair, he popped back up.
“Need anything?” he asked, gesturing towards my half full glass of crappy Prosecco.
“I’m good, thanks,” I said, my brows furrowed. We had a waiter…
He returned a minute later with a glass full of amber liquid. I’d later find out it was a double shot of whiskey, presumably to make it easier to interrogate me calm his nerves.
“So why did you get divorced?” he asked without missing a beat.
“Well,” I began, my Spidey sense tingling. I knew I was talking to a jilted man. “As sad as it is to say, we fell out of love.”
A horrified look crossed his face. “What do you mean?”
“We were 21 when we started dating,” I explained. “People change…?” It felt uncomfortable dissecting a relationship that had ended nearly a decade earlier with a perfect stranger.
No one invited you inside my past, Walter.
“Whose decision was it?” he pressed. Every time I thought the topic was spent, he found another probing question. “Did you go to therapy? How did you know he was unhappy?”
Before long, my insides screamed, I don’t want to be here! Walter later revealed that he’d had an engagement called off earlier this year, confirming my suspicions.
“I feel like I’m off my game,” I admitted about an hour into the date as I continued to falter from his inquisition.
Rather than offer reassurance, he replied, “Why?”
“The conversation got a little…intense.”
“I like to go deep,” he said and I fought the urge to roll my eyes. “You’re doing better than the one other date I’ve had here. She cried for most of it.”
Why am I not surprised?
“Yeah,” he went on. “I asked about her dating history, and she said she keeps getting used by men who wind up being married and just use her for sex because she’s ‘so good in bed.’ The only other woman I met since I moved here [earlier this year] was from Salem [three hours west]. She came to visit for the weekend and I had to work for part of it. Instead of exploring, she just sat in my living room the entire time. I was attracted to her, but that was such a turn-off.”
I nodded, my inner voice growing louder. I don’t want to be here!
I want to be here!
“A sense of humor is the most important thing,” he repeated several times throughout the night while not actually saying anything funny. “And how you reacted to the oven situation was a good test; you were really nice about it.”
Notoriously bad at exiting, the date lasted two and a half hours – which probably meant I passed another test. When we asked for the bill, the waiter automatically brought two separate checks. At least someone read the room tonight. I slowly took mine while Walter made zero attempt to intercept.
“Well,” I said, standing up. “Thanks for having your shit together.” It was the nicest thing I could conjure.
“Thanks for not crying,” he replied, inspiring my first chuckle of the night.
The next day Walter messaged me through Hinge, saying he’d had a good time. “It was nice meeting you,” I replied noncommittally. He then asked “what I was up to” that weekend without making it clear whether or not he was asking me out. I never responded.
When friends asked how it went, I told them the truth.
“The only thing turned on that night was his oven.”
Go Jules Go 