The Worst Dates We’ve Ever Been On

It is a truth universally acknowledged that in every friend group, there is one friend whose dating life more closely resembles the movie Saw instead of, say, When Harry Met Sally. If you’ve been that friend, well, our condolences. Also: We’ve been there.

Yes, much like you, we’ve been in the swamp that is the singles pool and waded through the muck, only to encounter men who reuse acupuncture needles and store them in their headboard, or women who have given us ecstasy, only to later reveal that there might be (read: definitely is) meth in it, too. The metaphor that finding love is like a needle in a haystack is perhaps not apt enough. We’d argue that it’s more like finding a vaguely smooth, nice-ish rock in a massive pile of shit.

Whether you’re still putting yourself out there or have given up on dating entirely (sure, this includes you happy fucks in fulfilling relationships), here are our collective dating woes.

I had a horrible first and only date in college that also happened to be my first date through a dating app (early adopter!) We chose to meet at 30th Street Station in Philly because I wasn’t yet 21 nor was I aware of things like “atmosphere.” The plan was to go to see his favorite band play a set in West Philly. On our way there, I asked what he studied, which opened a black hole into him talking about robots. I honestly don’t care about robots. In fact, I’d say I dislike robots. I don’t hold space in my life for robots.

Anyway, I’m a good date so I nodded along and asked followup questions for a solid 25 minutes. Finally, when he was done explaining robots to me, we walked in silence. A good date would boomerang the question back to me, asking what I studied. He was not a good date, so I offered up that info on my own. I told him I studied poetry, and before I could even finish that sentence, he said, “Oh, I fucking hate poetry. It makes no sense.” Then we continued to walk in silence to the venue where, when we got there, we stood in the way, way back. I asked if he wanted to move up because it was his favorite band, and he said no because he was “insanely timid.” I continued to run into him for years after that. —Kady Ruth Ashcraft

At first, it was good—so good that I texted him from the Mermaid Inn’s bathroom something like, “I’m having a great time.”

“Same :),” he replied from the table. For the sake of the night’s narrative, we should have ended it after dinner. Then it would have been a good date. It only turned into a bad date after, which trashed the night but spared my future from ever seeing this guy again. Bad dates can be good things.

After dinner we went to his friend’s place for drinks. I didn’t particularly want to do this or like the friend after I’d met him, but he lived at Union Square so I figured I’d stop by with my date before hopping on the L train back to Brooklyn. While I tiptoed up to drunkenness, they convinced me to go to a club with them—Marquee had relaunched and was temporarily hot (on Thursdays I think). Fine. We walk in and within minutes, two guys I’d hooked up with (separately) together said hi to me (I guess it was their night to hook-up). They were on some kind of something. My date did not like this. I don’t think I ever grasped what his rationale was—the interaction was brief and not overly flirtatious. I ran into two people in the club that I previously had sex with. It’s called being gay in New York, look it up.

Nonetheless, in response my date refused to talk to me, at which point I should have taken the hint to hang out with the friendly guys or, more sensibly, just go home. Instead, I pled my case to my date outside the club after begging him to meet me out there. At the time, I’d had a series of bad dates and connections that just wouldn’t cohere, and for whatever reason I needed to prove to myself that one could. After way too much effort, my date agreed that we’d continue our hang, only to become immediately incensed when my former hook-ups smiled at me or some kind or minor shit back inside the club. At that I finally took my cue to leave and never talked to him again. He went on to appear on a reality show with some notoriety. I did not.—Rich Juzwiak

It was the third date with a guy I admittedly didn’t really like, but he said he wanted to make me coq au vin, was tall, and had an incredible apartment. I figured, “Maybe he’ll grow on me.” We eat dinner, conversation is pretty boring and slow moving, so we pivot to the couch with some wine. We were both into edibles and he said he’d gotten a bunch of new ones, offering one to me. I, an idiot, took one without inquiring how many milligrams it was. He starts looking through Netflix for something to watch before settling on Dating Around, prompting him to give mean and shallow critiques of every single person on the show while explaining why he doesn’t think they’re dateable. I had not asked!!!

Somehow, I truly don’t remember what the connective tissue was here, he pivots to showing me a random hot blonde on Instagram. After scrolling through, showing me the screen, and saying, “super hot, right?” he tells me he dated this woman and that she ghosted him. At this point, I’m like, “okay, do you want to be on this date with her then?” He tries to backpedal and I realize my earlier error of not asking how many milligrams I’ve taken. I ask him for the bag and he obliges before continuing to scroll through Instagram. Around the same time that he finds a different woman that he once dated to show me (???), I learn the gummy I ate was 50mg BY ITSELF. I show him the bag and he tries to mansplain me, telling me I must’ve read it wrong. When he sees for himself that I’m right, we both realize we’re mere minutes from being on the fucking moon. I managed to get my shit and book it, only to get downstairs and feel the high taking hold.