The Worst Dates We've Ever Been On

Please enjoy these extremely unromantic memories we have compiled for your entertainment

PublishedFebruary 14, 2022

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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.

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2 / 10

I told him I studied poetry and his response was that he fucking hated poetry.

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

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3 / 10

We went to the club on our first date.

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

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4 / 10

He (accidentally) gave me a 50mg edible and then showed me his ex’s Instagram.

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.

The TL;DR is that it then took me 90 minutes and two Ubers (one of which was not mine...) to travel two miles from his apartment to mine. I woke up the next morning still extremely high and never spoke to the dude again. -2/10. — Jenna Amatulli

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5 / 10

I had to pay $200 to help him get his car after it got towed.

His name was Holden, he was very good-looking and seemed to be quite aware of that. He told me out to dinner. He had spinach in his teeth the entire time, which I wasn’t ever able to tell him because he wouldn’t stop talking about himself for long enough to let me get a word in.

We blessedly finished this dinner monologue and got back to my place, where he had parked illegally. There was a sign in front of his car pretty explicitly alerting him that he would get towed if he parked there, and indeed, his car had been towed! I accompanied him to the towing place, where he proceeded to argue that because this had happened on my property, I was responsible for the entire payment. I wanted him immediately out of my life, so I took $200 in cash out of the ATM, which I really could not afford to do at the time, and paid to free his car. Then he gently caressed my face and said, “Babe, I hope this doesn’t ruin things between us.” —Laura Bassett

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6 / 10

He wore a vest with no shirt under it at a fancy Italian restaurant.

I’ve only been on one date in my entire life, and the guy wore a vest with no shirt underneath and serenaded me in an Italian restaurant. He was a Broadway actor — smoking hot, super attractive man, unfortunately. I can’t remember what the song was, because I hate musical theatre. I left as soon as the bill came and never spoke to him again. It was the Olympics of embarrassment. —Mia Wilson

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7 / 10

He tricked me into taking him grocery shopping, then asked to borrow my pizza floatie.

When I was living in Westwood near UCLA, I had gone on a heavy Bumble dating craze right after college. I was pleasantly surprised to match with a man who was physically angelic, witty, and, most importantly, PHYSICALLY ANGELIC. After a few dates and some casual back-and-forth text exchanges, my heart exploded when he texted me to hang out on a week night. I asked what he had in mind, to which he responded, “How about we grab groceries?” I swooned as I imagined us playing boyfriend and girlfriend in the produce aisle, perhaps him pushing me in the cart in the parking lot and us giggling into the moonlight, only to cook pasta and make out later. Done.

I drove to pick him up because 1) he lived just a few minutes from me and 2) he didn’t have a car. He’d just moved from Denver, had sold his car to afford the move, and took the bus to work. Transporting my date was the least I could do, so long as we had our Lady and the Tramp spaghetti moment after. He teased me for grabbing a box of gluten-free pasta, and I felt very lucky that everyone in the store must think I’m dating this bombshell of a bro. As we hopped back in the car, he directed me to his place. I parked in the driveway, turned off the engine, and started to follow him in, when he paused and said, “Oh, actually, I’ve got a lot of chores to catch up on. But I’d love to see you soon!” He kissed me, and I got back in my car. I’d just been bamboozled into taking this motherfucker grocery shopping like a carpool mom. He didn’t even offer sex for my services.

We stopped talking shortly thereafter. Over a year later, he texted me asking if he could borrow a pizza-shaped floatie that was in one of my Bumble profile photos. —Emily Leibert

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8 / 10

We uncomfortably grieved together.

I wouldn’t exactly call it a first date, but at some point while “hanging out” with a man I had met on a dating app a couple of hours earlier, it was clear that we didn’t have a connection or much to talk about. Though, I felt it would be rude to just leave, and imagined he felt it would be rude to just ask me to leave. We decided to watch some Schitt’s Creek together, inopportunely queuing up “Carl’s Funeral” from season 1. In an attempt to make small talk, my brain inexplicably short-circuited and I asked this virtual stranger when the last time he attended a funeral had been, prompting him to ask me the last time I had attended one shortly after he answered. What followed was an incredibly uncomfortable grieving session with a rando from the internet over his late aunt and my cherished late friend. Ever since that fateful experience, I’ve pre-written a list of ol’ reliable ice-breaking questions on the Notes app, none of which are particularly fun or special, but are certainly better option. —Kylie Cheung

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9 / 10

I didn’t want to kiss him.

I didn’t want to make-out with the man who took me to a Dallas Mavericks game on our first date. I had a great time, but I didn’t have it in me to lead him on for more basketball games. I just didn’t want to kiss the man because I was in love with the woman with whom I am now living. He was so sweet, but he really had no chance. —Caitlin Cruz

10 / 10