A couple of years ago I set up a profile on OKCupid (as you do) and arranged a date with a woman who seemed a good match: around my age, occupied with intellectual concerns, pursuing a humanities PhD at a nearby university — all traits that landed her squarely within my highly selective wheelhouse.
We made arrangements to meet at a stuffy Northern Liberties watering hole. I arrived early (which is to say five minutes later than we’d planned) and found myself waiting another fifteen or so for her to arrive. This worked out in my favor, ultimately, since it bought me enough time to down a quick vodka & soda and loosen up a bit before she arrived.
When she did finally come I already had a fresh drink (now my second, which looked like my first, because I’m full of tricks) and I was seated at a chaise lounge within sight of the stairs that led to the second story bar. When she came up the stairs I knew immediately it was her (from her pictures, obviously), and she knew immediately that I was me, either because of my pictures or because it might have been mentioned that there could have been a remote chance that I’d be the guy reading a collection of prose by the late-18th century French symbolist poet Stéphane Mallarmé (sorry, world) or perhaps because of the way she recoiled when we first made eye contact, twisting her face into a pained look suggesting disgust mixed with disappointment, as if to see me in person had been to realize she’d been sold a false bill of goods. And she was not happy about it! (I, on the other hand, was mortified.)
This fraction of a second set the tone for the rest of the evening (which was to be predictably brief), and we soldiered our way through a single drink together (which as I may have mentioned was actually my second, thank god). She was not only visibly displeased with our little arrangement but went out of her way to make this as evident as possible: she was pissy, sour, and completely uninterested in making the best of this awful situation, something I was trying (and failing, oh so miserably) to do.
In short, it was the most excruciating half hour of my professional dating life. As soon as we both realized there was most certainly not going to be another round she started angrily protesting the inattentiveness of our (actually perfectly attentive) server (I guess because I was so off-putting that the bill had to be paid RIGHT NOW) and she got up and stormed off to the bathroom.
I took the opportunity to sneak over to the bar and pay up and ensure we’d both get out of there before she snapped, and when she stormed her way back she shrieked “Ugh when is our waitress going to come?” I politely informed her that it had been taken care of and we could both be on our way now. So we walked out together. I lit up a much-needed cigarette and was pleased to see her do the same since at least this was one thing she wouldn’t be judging me for.
We said our goodbyes and then awkwardly/uncomfortably started walking in the same direction, which prompted her to ask why was I “following” her, which prompted me to curtly reply that I have to take the train in the same direction you do, THANK YOU VERY MUCH, which she followed up with a confused and stumbling recognition of the fact that we were now committed to three more subway stops together and that’s when she demonstrated a sudden change of heart, because she started talking this nonsense and tripping over all her words as she said “Oh so we’re going home together! I mean, er, I don’t mean “home”, “together”, I mean, no, of course not, that would be just awkward! Because my brother is in town and all, but I mean, you’re right on the Blue Line too, and your place is right there, and you live alone, and I mean…” — and this is when my heart stopped, because here we were, only moments after the single worst dating disaster I’d ever survived, and this genuinely horrible person who only thirty minutes earlier went out of her way to make it abundantly clear that she thought I was completely horrible got it in her head that hey, you know, she didn’t mind a little slumming, so now we were going to sneak away for some quick casual sex.
And I was going to have none of this, clearly, but by now I was totally defenseless since the train doors had already closed behind me and I was trapped in a subway car with a woman who legitimately terrified me and I had no idea how I was going to escape this situation because the logistics just didn’t line up in my favor at all: her stop was before mine, which meant if I didn’t explicitly rule out the possibility of sex before reaching Broad & Pine, I’d have a real problem on my hands by the time we reached Broad and Locust together. Meanwhile, the train pulled into the Market Street stop, and in a brief flash of genius I hatched an escape plan: I thanked her for a lovely evening but told her I must be getting off now because I’d forgotten something at my Market Street office.
I fled with just enough time before the doors closed but with plenty of time to turn around and bask in the look of shock on the face of this awful woman who couldn’t believe she’d just been denied a booty call. As I darted up the station stairs towards freedom I smiled fondly at the thought that this look on her face was the last I’d ever see of her.
The next morning I received a cold, formal email saying she was very sorry but she didn’t want to see me again. “Sometimes people just don’t click,” she told me.
I actually laughed out loud.
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