All The Times I’ve Run Into My Failed OKCupid Dates


It’s difficult to know where to begin exactly, or with whom, because there was a stretch of time — maybe like, 2008-2010 — in which I dated men from OKCupid with a frequency more commonly reserved for, I don’t know, urinating. The following accounts might not make sense chronologically, but if you think about it, does time or anything make much sense?

Andy, we can start with him. He didn’t live in the city yet but almost, and he was my type — not the type I always actually, legitimately find myself dating, but the type I imagined in my head when I was a little girl, before I understood things like personalities and emotional chemistry; the type whom my friends see photos of and say, “You have such a type.” If you’re curious, my type is this: tall, thin, brown hair, looks great in sweaters, wears glasses because he reads a ton, probably. The people I end up dating, well, they’re people, not types. Back to Andy.

Our dates were fun, but the friendly kind of fun. Drinking, yelling, taking shots, laughing big. We went out three times I think, but not once had our dates been punctuated with a kiss (though we had flirted; though he had paid; though we’d been caught in a rainstorm together; though I’d met his coworkers; though after our first date I happily watched him from across the subway platform as he slipped into his train, watched through the tiny window until his face blurred into nothing, disappeared through a tunnel; I was smiling smiling smiling). I remember deciding that if he didn’t kiss me at the end of our third date, we were probably just friends except to be honest, I was okay with that and with other alternatives, like never seeing each other again.

And we didn’t see each other again, until a year later when I was walking to the subway station and saw Andy headed in the same direction. I ran over and said hello — he had been staying in New Jersey when we met, but now he was here, living, like he’d told me he would. “Hey!” I yelled, and I gently tapped or pushed his shoulder. “You made it down here!” Andy introduced me to his roommate and we decided that since we were kind-of neighbors, the three of us should get high together sometime, although this never happened, like most things.

The next time I saw Andy, I was at the supermarket with a guy I loved and Andy was there with a blonde girl he loved but, on that particular day, at that very moment, the guy I loved and I were in a silent way, and Andy and his girlfriend shared the kind of laughter that sounds like juggling oranges — loud, bright, heavy, golden — and so I hid that time because I wanted them to have whatever moment they were having in Aisle 3; if people are having that kind of moment, you should just let them.

I saw Andy and his girlfriend again — they’ve probably been together for two or three years, at this point — they were crossing the street with huge backpacks on, the kind you travel with. I wondered if they were coming or going, and where, but didn’t ask or even say hi. I just mostly felt an empty hole where the jealous part of me should have been.

After an early-evening date with Andy one night, I did a morally questionable thing and went on a second date with an OKCupid user named Eric. My intentions weren’t nefarious, I was just dating often back then and going on two dates back-to-back was the most efficient plan for all involved parties. I was exhausted after the first date and had some work on my mind — a six-page list of different kinds of “bitches,” penned by a third grader, had gone viral and it was my job (LOL) to come up with additional “bitches” to add to the list. After I shared my dilemma with Eric, we found a booth in the back of the bar and dreamed up bitches together. We coined “acrylic nail bitches,” “give a penny TAKE A PENNY bitches,” and “dial up modem havin bitches.” As with Andy, Eric and I had a great time but it was more of a bro-out than a date. (This is pretty much par for the course for me; it’s confusing but also not the worst thing that could happen.)

The first time I saw Eric out in the wild was the same day I saw Andy walking to the subway with his roommate. Actually, it was the same moment — the three of us were walking down the street together toward the same subway station like we were starring in some mumblecore film titled Seven Degrees of OKCupid. While I played the part of Well-Adjusted Human when speaking to Andy, I dodged Eric completely, because… I don’t know? What is the proper etiquette for when you run into someone you got drinks with one time and then announced to one another, via non-action, that you’re never going to purposely hang out again? Furthermore, what’s the etiquette for when you run into this person while conversing with another failed OKCupid conquest?

I learned there is no etiquette for these situations, there is only feigned ignorance. Eric and I saw each other again — once he served me drinks at a community-based art show, although by that time there was no freaking way he would recognize me (I have long brown hair and bangs, after a while we all start to look alike). More recently, I noticed we were walking down the same sidewalk so I crossed the street (I was carrying a ton of groceries, which I’ve learned is the perfect activity to partake in if ever I want to appear like I’m about to keel over and die). And on Saturday, I saw him in Walgreens while picking up my birth control. It was the worst of times, it was the worst of times.

There were others. Take the guy I’d agreed to meet almost immediately after a breakup (who I then canceled on because I was too damaged to function). Turns out, I recognized him at a bar a few months later and told him I felt horrible about canceling, could we reschedule? (He agreed to what would manifest into yet another bro date where we were more interested in maximizing our happy hour than we were in each other.) I see this guy on a monthly basis (not on purpose) because he is everywhere. He is more everywhere than GOD. The laundromat, Internet Week, my local bar — my neighborhood is like an elephant graveyard for failed OKCupid dates.

Why can’t I just wave and smile like a normal person? The answer is that I do, for the most part, when it’s appropriate. Like, when the guy isn’t with his girlfriend; or when I’m kind of sure he won’t be like, “Who the hell is this smiley, wavey bitch?” But other times, I just can’t feed into the small-talk machine. I don’t remember anything about these people, occasionally I don’t even remember their names. If we had anything of value to say to one another, we’d be dating — not running into oncoming traffic to avoid that awkward, “do we owe each other this?” conversational dance that no one in the history of ever is comfortable having.

For a number of reasons, I’m out of the online dating game for the foreseeable future. It may be lonelier, but it beats the hell out of frantically maneuvering through gridlock with 20 pounds of groceries in my arms.

You should like Thought Catalog on Facebook here.