My Year Of OkCupid: A Retrospective


As inauspicious beginnings go, my entrance into the world of online dating has a place in my personal Hall of Fame.

That’s because I slept through it.

I’m not aiming at metaphor here. Eggs Benedict and a few too many mimosas at a late brunch, not to mention the three rounds of “pancake shots” the server gifted us in order to ingratiate himself with the four women at the table — well, the next thing I knew, my postprandial catnap had become a brief coma, undisturbed by my date’s increasingly frustrated text messages. I overshot the runway of my own alcohol tolerance by more than an hour.

It could have ended there, and not just that particular date. I could have raised the white flag on my entire foray into the wilderness of OkCupid before it even began, chalked it up as a message from the fates that the days of set-ups with friends of friends were not yet at a close. But I didn’t. Instead, I called him back and threw myself on my sword. I apologized profusely, and sincerely, for being an asshole. I said I’d probably tell someone who did the same to me to fuck off. I made clear that I would understand if he did so. I offered to try again, if he were willing to give me a second chance.

When I stirred awake in his bed the next morning I might have taken it as yet another message, a premonition that my year of OkCupid would be, romantically at least, my year of living dangerously. But you will have figured out by now that reading the signs is not my strong suit.

If you should ever want to see what your friends look like while experiencing pity — especially if those friends are shacked up, engaged, married, or otherwise committed to a significant other — perhaps the easiest way is to tell them you signed up for a dating website.

Few, if any, will say it aloud, but even your most supportive friend will not be able to prevent the unspoken sentiment from flickering across her face. “Whoa,” you imagine her thinking. “I had no idea it was that bad. But I guess if he’s out of options…”

This is your life now. You’ve contracted a terminal case of singles. Grindr, with its thin veneer of civility — if you really wanted “networking” you’d have signed up for LinkedIn — may have lessened the stigma, at least for gay men. Against an app full of headless-torso selfies “looking” for Mr. Right Now and Standing 300 Feet Away, the photographs attached to my online-dating profile, all smiles and conservative cardigans, seem positively prudish. Even so, if you are not 44, divorced, or paying for the privilege, online dating might seem to mark you as damaged goods, and creating a space for others to evaluate you as a potential partner is a harrowing confrontation with the person who’s caused every break-up you’ve ever had: yourself (see Appendix A).

Each OkCupid profile is, in this sense, part autobiography, part argument, and part fiction. It requires that you make yourself legible to a stranger in a few paragraphs, a handful of vital statistics, and innumerable either/or questions seemingly designed to test the human pain threshold as least as much as your compatibility quotient. Even if every word in it were technically true — a feat of conscience that would render you incompatible with me — he who composed a full accounting of himself without lying by omission would be a pitiful date indeed. In other words, there is a man on OkCupid who shares my face, my interests, and my conservative cardigans, and his name is “Matt Brennan.” But he’s not quite me.

There is, from time to time, another person sitting on the other side of the table, or at the next stool down the bar. The arrangement of this first encounter can seem like a pre-requisite for enrollment in the Foreign Service. The negotiation of where and when to meet demands a series of deft diplomatic maneuvers, not to mention fluency in what can seem another language:

“Where do you want to grab a drink?” I’m deferring to you even though there’s a decent bar two blocks from my house.

“I’m pretty flexible, what do you think?” I’m paralyzed by indecision.

“Have you ever been to Bar X? I love that place.” This is not the bar two blocks from my house. If we go to the bar two blocks from my house and I invite him to come over afterwards, it will seem like I’m a big slut who planned it all along.

“No, what’s it like?” I refuse to go to a place where they only serve PBR tall boys and Jim Beam.

“It’s a bit of a dive, but the drinks are cheap and it won’t be too loud on a weeknight. There’s also this other place, Bar Y, with great cocktails.” I’m hedging my bets, and now if we end up at the bar two blocks from my house (Bar Y), it’ll be his fault. Not my decision!

“Bar Y sounds great, I’ll see you there!” Bar Y is pretty good, I can live with that. I wonder if he suggested it because it’s in his neighborhood…

This, the first date, is the romantic equivalent of a high-pressure free throw in the closing minutes of a basketball game. At this moment the “technique” — the learned experience of what questions to ask, what clothes to wear, what drink to order — becomes instinct, and the success or failure of the endeavor hinges upon your ability to take a deep breath, let go, and not flinch.

As in sports, the outcome is an omnipresent barometer, and in retrospect I might plot the success of those first dates on a long-term axis: the engineer in the baseball cap who never called; the actor I kissed on the street corner before he moved to San Francisco; the dog-lover I saw for two months and the poet who replaced him. In the moment that it’s happening, though, the finite, controlled space of a first date achieves something like purity, already always full of promise. I remember now that the aforementioned poet and I were interrupted by an inebriated couple — “You’re on a date?!” the woman squealed. “How cute! Joe, they’ll have to invite us to their gay wedding!”

Without exchanging a word (like I said, instinctively), we decided to engage them. The evening turned seamlessly into two conversations, and when Joe and his girlfriend settled up for the night I realized that my date and I had barely spoken. But we knew everything about each other that we needed to know. That I found this terrifically sexy may have been yet another misreading of the signs. I should have realized, though of course I did not, that the dangers involved in my year of OkCupid might extend into the realm of the emotional. But at the time I was only concerned with how exhilarating it felt to realize the goal of the first date: no longer to write a better self but to make the most out of the self you have.

As you may have gathered, there was no gay wedding for Joe and his girlfriend to attend. I never expected one. In fact, I think my problem was that I never expected anything. I never expected to have such trouble breaking off a brief relationship. I never expected that someone I was dating would aim the L-word, “love,” in my direction. I never expected that I would be introduced as the boyfriend one week and find myself single again the next. It was after this last occurrence, my year of OkCupid nearly over, that I met someone “in real life.” Having convinced myself that online dating was to blame for the false starts of the past twelve months, it came as a bit of a surprise when this, too, failed. One more thing I never expected.

Online dating has taught me any number of lessons — don’t get drunk and fall asleep before a date; inviting someone back to your place to “borrow” a book you’ve been talking about actually works — but the most important may be this: people who say online dating will irrevocably change the way we interact, for good or for ill, are missing the point entirely. Online dating won’t save you, and it won’t ruin you, either. It will only force you to navigate, using different tools, the same treacherous terrain dating always does. I could blame the frustrations of online dating or I could blame not meeting enough people in “real life,” but in the end the blame fell upon the unifying factor in all these encounters. Me.

That it took me a year of OkCupid to understand this may not suggest a high-powered intellect. Frankly, it’s embarrassing. But the realization has been a liberating one. With the responsibility on me — not the cosmos, not gay bars, not OkCupid, not you — it’s much easier to accept the course of events. It’s a kind of control that feels blissfully like the opposite of living dangerously.

Now that I know what to expect, I’m trying to date again. I recently met an actor for a drink after exchanging a few messages on OkCupid. A colleague from work is trying to set me up with a friend of his. I still write messages with abandon, and warm up with a drink or two before the first date, and try as far as possible to avoid being an asshole. I’m still waiting on the right sign to come my way. Here’s hoping I’ll know how to read it.

Appendix A: How My Profile Would Read If I Were Being 100% Honest/(My Actual Answer)

Ethnicity: White (Same)

Height: 5’9″ (Same)

Body Type: Did I really put on this much weight since college? Shit. Isn’t there anything between “Skinny” and “Average”? (Skinny)

Diet: Never tried one. (Anything)

Smokes: If you want to get technical about it, I’m smoking right now. But I’m considering thinking about quitting soonish, so really if you think about it I’m basically trying to quit. (Trying to quit)

Drinks: Two-buck Chuck and too much bourbon. Oh, I get it now. They want to know how frequently I drink, not my Old Fashioned recipe. Well, if Mad Men is on, you’re not really drinking alone. (Socially)

Drugs: Man, that concert last weekend was so much fun! It doesn’t allow you to specify what type of drugs, though. Does this photo make me look like I smoke crack, or just pot? (Never)

Religion: Strident atheist. (Left blank)

Sign: If you really care about this, you won’t like me anyway. (Aquarius but it doesn’t matter)

Education: Phew! I thought we’d never get to the questions that don’t make me look like a walking hurricane of maladjustment. (Working on Ph.D program)

Job: People definitely think writers are sexy. (Artistic / Musical / Writer)

Income: People who know how much writers make definitely don’t think writers are sexy. (Left blank)

Offspring: I am not a fucking wolf, the word is “children.” (Left blank)

Pets: It’s not like I would never have a pet! And you dog people are crazy about dogs! And if I eliminate all the dog people right off the bat, I’ll never get a date! (Left blank)

Speaks: Too much for his own good. (English, French) Thought Catalog Logo Mark

image – Johan Larsson

More From Thought Catalog