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8 People on Their Most Disastrous Flirting Attempts

Photo-Illustration: The Cut; Photos: Getty

Flirting is an art. And art can be bad. It’s not easy to make a move that is both mildly seductive and socially acceptable. There’s no guide to putting out a vibe that says, “I like you,” but also, “I’m cool, and not desperate.” Sometimes, a botched flirting attempt can be charming; other times, it’s an endgame. From accidentally insulting someone to misreading the whole situation, here are eight stories about flirting disasters.

“He didn’t look at me once for the rest of the night.” — Laura, 32

I was at a music festival and had VIP tickets through my journalist friend. We’re at this hotel suite party, and I’m hanging out with my favorite band of all time. I won’t say who, but they’re a British band, and they’re a bit older and all totally hot. The drummer is kinda flirting with me — and by flirting, I mean, talking to me, and I’m flirting with him (laughing, trying to sound interesting, praying I looked cute). I love drummers — it’s a problem. They are usually bad news. I have a bit of cocaine on me, which I use as an excuse to get some one-on-one time with the drummer. I’m like, “I have coke … wanna go to the bathroom?” Yep, that was my pick-up line. He’s like, “Fuck yeah!” Now I’m kind of freaking out; it felt surreal. I was sure we were going to have sex in there. We walk into the bathroom, and I hand him the little baggie of coke. I sit myself up on the sink, trying to be as flirtatious and seductive as possible. He takes the bag of coke, says, “Thanks babe!” and walks out of the bathroom without me, closing the door in my face. He took my blow to all his friends to party with and didn’t look at me once for the rest of the night.

“He turns to me and literally says, ‘That’s a bit judgy.’” — Cara, 49

I was standing behind a really cute guy at a coffee shop. The line was long so we had a chance to chat. He was adorable — kind of had that Mark Ruffalo look. And no wedding ring. I’m trying to strike that balance between flirting and being normal. It’s going well. We talk about the neighborhood and our dogs. Then I try to get witty and show him that I’m a funny girl, and I say, “Don’t you think there are too many milk options? I mean, really, who needs fucking pistachio milk? It’s so embarrassing!” He turns to me and literally says, “That’s a bit judgy.” And then he turns around, orders his pistachio milk latte, and we completely stop talking.

“Suddenly he’s like, ‘What the hell? Get off me!’” — Georgio, 40

I was at this very gay Halloween party last year. I went in drag, of course. My long-term relationship had just ended, and I was fuzzy in the flirting department. But I was super-horny and wanted to find a man to have sex with. I see this guy who’s my type — very pretty, very cute, very petite. I walk over to him. It’s super-loud in there, so it’s hard to flirt, and I honestly don’t know what to say. So I start by introducing myself. Then I ask, “Do you want to have a smoke?” thinking we could go outside and share a cigarette and chat. He says, “Sure.” I take his hand to lead him toward the front door of the bar. I’m pulling him, and he’s not moving. So I yank his hand a bit hard, thinking he’s just being playful. Suddenly he’s like, “What the hell? Get off me!” His hands are flapping as if I’m abducting him. His friend intervenes. I was like, “I asked him to go have a smoke, and he said yes!? What is going on?” The guy thought I said, “Do you want tickets to my show?” As if I would ever say that as a pick-up line. It was dramatic and awkward, and I just felt stupid by the end. I left the party alone.

“Then she said, ‘You’re really pretty but I have to be honest …’” — Rachel, 28

I met this woman at a yoga class. She was very beautiful, so I was watching her the whole time I was supposed to be working out, and I was rehearsing my pick-up line when I should have been being mindful or present or whatever. After class, I went over to her to bullshit about the class and her “yoga practice.” She said she liked this place because it was so queer-friendly, which gave me the green light to flirt a bit more intensely since I’m queer as well. I went for it. I said, “Hey, maybe we can have a drink sometime? If you drink alcohol … I mean, tea is okay too. I love spicy margaritas personally. But whatever, I’d love to take you out. Like on a date?” It was awkward the way it came out, but I thought it was possibly awkward in a charming way. She smiled and for a second I thought everything would be okay. Then she said, “You’re really pretty but I have to be honest, your energy just seems off.” I was like, “Cool …” What does that even mean? Like, my energy sucks? I wrote her off as a total weirdo.

“We both ignored it until the smell went away.” — Jenny, 32

I was at a friend’s wedding rehearsal in Connecticut, and I was flirting with a guy who was friends with the groom. The night started at this beachside bar for cocktails, and then everyone was getting themselves to another location for a dinner party. Anyway — the guy and I met at cocktails, we shared a little conversation about how Waspy the scene was, and we both registered that the other was not Waspy, attractive, and single. But it was time to move on to the next part of the night at a new location. So he said to me, “I’d love to get to know you better at the dinner party … make sure we hang out!” I’m like, “Totally.” I get in my car to drive to the next location which is about ten minutes down the road, and when I get in my car, I let out an epic fart. I think the apps at the cocktail hour messed up my stomach. It was so gross. A second after the fart, he knocks on the window of my car door. He’s like, “Can I ride with you?” I died. He got in the car. I said, “Um, there’s like … a dead rodent in my car somewhere, I think … I’m so sorry.” We both ignored it until the smell went away. We ended up getting wasted and hooking up that night. Then I never saw him again.

“I just thanked him for the drink and moved on.” — Tony, 55

I met a guy at a bar. We were both grabbing a drink before our own online dates (with other people). I was all, “Dating sucks.” And he was all, “Dating sucks.” And for a moment it all felt super-fateful and romantic to be meeting like this and bonding over New York’s gay dating scene. He bought my drink and was super-chivalrous — like, he stood up when I’d get up to use the bathroom and when I came back. So I said, “Your mom raised you right.” He replied, with a tinge of anger, “My mom is in jail.” So, I said, “I mean, your dad raised you right!” And he said — again, pretty bitter — “My dad is in jail.” I didn’t really know where to go from there. I was going to say, “Three cheers for Grandma?” But instead, I just thanked him for the drink and moved on to my next date.

“I was getting a bit tingly just thinking about what this could turn into.” — Meg, 42

I was taking my first SoulCycle class — totally late to the game. But I was also just out of a divorce and trying new things. One of the other new things included dating women as well as men. So, there’s a woman getting on her bike next to me, and she looks like she’s probably a lesbian. And I’m attracted to her. I ask her to help me set up my bike, and she’s super-helpful. She even gets me on top of my bike and locks my shoes in, etc. There’s physical touch and in my opinion, we were flirting and it was erotic. I was getting a bit tingly just thinking about what this could turn into. Then I said to her, “Do you like this teacher?” And she says, “Um, my wife does.” And that was that.

“I got some gum and avoided him the rest of the night.” — Martina, 29

Oh, this is so embarrassing, I’ve never repeated it before. I went to a restaurant opening party with a friend. I was coming from work, and it had been a long day, and I barely had time to eat. On the way there, I had a protein bar. I forget the brand, but it’s the kind that is very sweet and chalky and fake-healthy. Anyway, at the opening, there were a lot of cute guys. I started talking to one. I was like, “What’s your connection to the restaurant?” (Mine was that my friend ran their marketing). The guy looked adorable but was acting really standoffish, really aloof. He was answering me in one-word answers. I keep trying. I double down. I ask more questions. “Do you like this kind of food? Are you a foodie?” That kind of thing. Finally, he says to me, “What did you eat before you came here? Your breath is really funky. It’s making it hard to have a conversation.” It was the fucking protein bar! I was mortified. Also, what an asshole. I got some gum and avoided him the rest of the night.

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8 People on Their Most Disastrous Flirting Attempts