A Decade’s Worth Of Very Weird Dates


I have been dating for about 10 years.

I don’t know how many dates I’ve been on, but there have been more than enough for me to draw the conclusion that I don’t really like dating all that much.

Why? Well, in short, dates—especially first dates—have a tendency to be strange, terrible and/or awkward as fuck. At least in much of my experience.

Here are a few of the more memorable occurrences that have made me question my desire to not be an agoraphobic asexual.

1. I took a friend who I was attracted to on a date for New Year’s Eve. She got really tanked on sangria, to the point she could barely stand. I hailed a taxi and took her uptown to her home in Harlem. As I was tucking her into bed, she told me she loved me. I did not know how to handle this information, so I told her we’d talk in the morning. I left. As I was standing on a street corner some dude called me a “white motherfucker” for no reason other than he probably thought I was one of those white motherfuckers trying to gentrify his neighborhood.

2. The date was already awkward when the girl asked if I dug Thai food. Instead of copping to the fact that I’d never had it—I didn’t want to seem uncultured—I said I loved it and took her to a Thai place nearby. When I had no answer to “What do you usually get when you eat Thai?” she realized I was a fraud. It was even more awkward after that. A couple weeks later she was back with her ex-boyfriend.

3. I had sex with a girl on a first date. Then I had a vivid sex dream about my ex-girlfriend from forever ago who I’d not slept with in about three years. I woke up very confused, and the first date girl asked me who Beth was. I told her I wasn’t really close with anybody named Beth. I spent the rest of the morning staring at the ceiling wondering what in the fuck is wrong with me.

4. I ripped my jeans in the crotch as I ascended the subway steps toward my destination. I was too close to turn back and too short on time to buy a new pair of jeans, so I just went with it. I probably should have addressed it immediately, but she didn’t bring it up, and so we plowed through two rounds of drinks before she asked me what in the hell was up with my pants.

5. I got pretty drunk on a first date and there was certainly a strong physical connection with the girl. I realized this when I drunkenly noticed that, in the middle of the bar, she had unbuttoned a couple buttons on my shirt and was pinching my nipples while she kissed my neck.

6. Earlier this year, I met a lovely woman named Shannon on OkCupid. We messaged back and forth for a while before exchanging numbers and eventually deciding to meet. We had a nice date, kissed at the end, talked for a while after, etc. But we never could get it going after that because our schedules were very disjointed. We kept in touch, though, and she kept me abreast of her mating situation, which was that she had started dating a guy form her past. Months after our date, she texted me to tell me she thought I was a great guy and that her younger sister was newly single, and would I be interested in meeting her sister? I was like, sure, why not, it’s not like I’m over here drowning in pussy or anything. So I meet her sister, it goes really well. We go on, like, four dates. During the fourth date, sister reveals to me that she was shopping for dudes for Shannon on OkCupid when she found me, at which point she proceeded to engage. I was messaging with the younger sister—who was in a relationship at the time—until the point of a phone number exchange (like 10 or so messages). Younger sister also catalyzed the text from older sister about meeting up after she found herself back on the market. Younger sister and I went on a few more dates before a tacit agreement was met where we decided that our schedules were too erratic to see each other often enough to keep putting any effort into it.

7. A woman I had met less than 60 minutes earlier borderline chastised me for never having tasted my own semen, and insisted that I try it for empathy reasons.

8. I told a woman she could ask me anything she wanted, that I was an open book, and she asked me which part of a baby human I would eat. This came shortly after I had shown her a photo of my newborn niece.

9. A girl came home with me after a nice night. We had sex. The next morning, she revealed to me that she was not on birth control. I then revealed to her that I had faked an orgasm.

10. I involuntarily wept my way through the second half of “Marley & Me.”

11. I walked into a bar and accidentally approached the wrong girl. The girl I was supposed to meet walked into the bar as I was explaining my folly to the other girl, who, in hindsight, I honestly would rather have spent the night with than my actual date.

12. While on our first date, a woman revealed to me that she worked as an escort, but was off the clock. When she registered the look of shock on my face, she said, “What? At least I’m not a mom.”