Dating, humor

Dear Newly Single Men: Please Stop Doing This

“Have you ever seen Gary Gulman’s stand-up bit about finding a $20 bill in your coat pocket?”

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.


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.


“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 onĀ 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.