Online dating is great for people who don’t spend too much time online: outgoing people with active lifestyles who work demanding hours and don’t have time to meet people anywhere other than the Internet.

…and when I did online dating, those were the type of women whose profiles I was attracted to: the ones who seemed to have their careers and their personal lives together, but just didn’t have time to go out and find that right guy. I always swiped left on women who seemed too desperate, especially if it seemed like they were just messaging every guy whose profile they saw and weren’t particularly drawn to mine. I imagine a woman would have done the same.

It’s ironic, because at the time, I was so desperate. I was still waiting for the courts to finalize my divorce and still rebounding from the volatile off-and-on relationship with the woman I dated after separating from my wife. I was buying first-date-dinners at 5-star restaurants for women I had already judged to be way out of my league…based on the personae they had put forward on their profiles. A lot of them turned out to be losers, but who was I to judge?

Well, three months and 20 first dates later, it was February 13th, and I didn’t have a girlfriend. I had a few women I had been out with once and had intentions to see again, but nothing serious enough to merit making Valentine’s Day plans. (Actually, the previous year, I had made Valentine’s Day plans with a woman I’d been casually seeing, and it was a disaster. More on that later.)

But there was one girl left, kind of a Hail Mary pass, where I felt like I had nothing to lose and got way too stupid.

She had peeked at my profile a couple times, and I didn’t know what to make of it, because she lived over an hour outside of Los Angeles without traffic (she’s asked that I not say which direction or the name of the town, so to protect her identity, let’s call it Mariposa Hills, just to totally throw you off).

Her profile also didn’t look real, because she had a sexually suggestive username and looked like an Eastern European supermodel. I had been catfished by profiles like this before, and I knew not to be fooled. But a week later, she peeked at my profile again, so I looked back at hers and was pleasantly surprised. She was a doctoral student with a degree from an Ivy League university, but also very into weight-lifting and smashing the patriarchy. Smart, active, and woke.

…just like me, right?

I messaged and asked her about her username. She said it was the name of a feminist group she belonged to. She asked me, and I quote, “How did you get into Feminism?” That question made me uncomfortable because I never thought of Feminism as something that people “get into.” It’s just part of being a good person: you either believe women should be treated equally or you don’t.

She told me how she was writing a book about all her dating horror stories. She said she liked dating men in L.A. because the men in Mariposa Hills were “so basic.” That was hilarious to me, since women in L.A. say the same thing about men in L.A. (Yet they still date men in L.A.)

Like me, she got married way too young. Like me, she got trapped in an abusive relationship right after leaving her spouse. And like me, she seemed to have a lot of first dates that went nowhere.

So now we were both teachers, and we spent our evenings neurotically checking our phones, sifting through potential profile matches and swiping right until Tinder told us our free trial was up. Whenever I texted her, she would text back immediately. Whenever I looked at her profile, she would look at mine. Most women only check their OKCupid profiles every couple days because it gets so overwhelming; she was on it all the time.

She asked me if we could talk on the phone. It’s very rare that a woman wants to talk on the phone before meeting in person, but I guess when the woman lives all the way in Mariposa Hills, talking on the phone is something you have to get used to.

I could tell she was very shy. She wanted to meet me in person but felt guilty about asking me to drive over an hour for a first date. I was breaking all three rules: a first date should be (1) local, (2) cheap, (3) quick. Ours was taking place 100 miles from where I lived, costing me a full tank of gas, and lasting the entire day.


We were meeting at 9 AM on Saturday for Bloody Marys. Waking up at 7, all I had time to do was throw on a polo shirt and brush my teeth. I didn’t bother wearing lifts, nor did I have time to shave, clean my car, shower, put product in my hair, or any of the other things I usually did before a first date. What was the point? It was February 13th and I still didn’t have a girlfriend. And it seemed like trying too hard, spending too much time on my appearance or spending too much money by dating out of my league, wasn’t getting me anywhere. So I just decided to relax.

…kind of. I mean, I was still crazy enough to drive 100 miles for a first date.

Speaking of which, it was 7:35, and our reservation was for 9:00. I had less than an hour and a half to drive 100 miles. Not looking good.

I was making decent time when, around 8:00, I looked up from my lap and saw a cop car shining his lights behind me. I slowed down and, seeing that there was nowhere to pull over, got off the freeway so I could stop.

Great, this was the most unnecessary first date I’ve ever been on, and now this ticket is about to make it the most expensive first date I’ve ever been on.

“Reason I stopped you is because of your speed,” the officer told me. He didn’t show me a radar reading, but he seemed pretty confident. “What’s going on? Why are you driving so fast?”

“I’m driving to Mariposa Hills to meet a girl because I’ve exhausted all my dating options here in L.A.”

He was just as taken aback by my words as I was by the fact that I had said them. Did me being single and desperate mean the law didn’t apply to me? Of course not. I expected him to snap at me, give me a lecture about how I was putting people in danger because of my own selfishness.

“License, registration, and proof of insurance,” he said, calmly.

I burrowed through my messy car trying to find the plastic envelope where I kept these things specifically for instances like this one, and as I opened the glove compartment to look for them, out popped a copy of my divorce papers, which had come back from the court rejected for the third time. I handed him the documents he was looking for, but of course, he saw the other, more embarrassing documents, and was probably about to have a good laugh at my expense.

“So do you live in Sacramento?” he asked.

“No, but I’ve changed my address with the DMV.”

“OK, but you don’t have a card saying that,” he sighed. “I’ll be right back.”

I sat in my car for ten minutes, waiting for the end result. This was bad. I had just gotten a ticket a few months earlier for not stopping at a crosswalk. I had just paid an exorbitant fine. And that was in San Bernardino; this was in L.A., where ticket fines are at least $100 more. Plus, I wouldn’t be able to go to traffic school this time. It was over for me. Everything was about to get way more expensive, all because I had decided to throw a dating Hail Mary after feeling self-conscious and desperate about the fact I was single on Valentine’s Day.

Ten minutes later, the cop reemerged at my car window.

“I’m giving you a verbal warning.”


“Watch your speed. What’s your girl going to think if you lose control and don’t make it to your big date?”

Is this a joke?

“Thank you, officer,” I replied as he walked back to his car. He looked happy. Maybe he felt like he had done his good deed for the day, or maybe he was just laughing at me. Either way, I was very lucky, and I hoped this good luck would continue through this very risky meeting with the Ivy-League SJW weight-lifter.


3 thoughts on “The Day Before Valentine’s Day: Single Guy Edition

  1. You describe yourself as “woke” but shame women for being foolish enough to date you on the internet?

    You are so not woke, pal.

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