Know Thyself…Maybe.

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.”


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’ve definitely had some creepy things happen,” I nodded. “Statistically speaking, women are far more likely to be abused and killed by men they know, as in, in a romantic context.” Seriously, dude? Have you seen any Netflix documentary, like, ever?

“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.