Love & Sex

Fifteen Ineffective Pick-up Attempts

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Our readers sent in stories of romantic overtures gone wrong. We picked our favorites.

I was flirting with a business guy at the bar where I cocktail, because that's what cocktail waitresses do. When he left, he made a big deal of handing me his signed receipt. I thought he had left me a big tip. Instead there was a name, phone number, and the phrase “I want to play with your tits” written — bafflingly — in Spanish. — Kelly


I was at a big warehouse party and approached a young gentleman waiting outside the bathroom. “Are you in line?” I asked. He said no. When I came back out of the bathroom, he was still waiting. “You’re still here.” I said. He nodded forward, a bit drunk, and shouted, “I was going to follow you in, but I figured it would be rude to all these people waiting in line,” just as the song dropped off. Everyone in earshot laughed.


My coupled friends are always trying to get me laid, either out of affection or just to get me to shut up about being sexually frustrated. I went with friends — a married couple — to a restaurant and the three of us flirted with the waitress shamelessly. Then at the end of the night, they wrote my name and phone number on the twenty we used to tip her. When they told me (after we'd already left) I said, "You guys are adorable, and also it's clearly been a long time since you've been single." — Peter


One day, a giant bouquet of roses arrived at the restaurant where I work. My boss said they were for me; I ran over, practically glowing. Until I saw they were from Timmy — an unattractive, older regular. Not only was it less than flattering, Timmy was also notorious for bringing crazy gifts for his favorite waitresses — Chanel boots, Prada heels and so forth. One of my coworkers had hawked his gifts on eBay to pay her rent. No such luck for me — it was the day after Valentine’s Day, when leftover roses sell for fire-sale prices. — Lina


Once, before my English was very good (I’m Hungarian), I went up to a girl I’d never met, handed her a single red rose and said “You are so very attractive." She left, nearly at a run. — Andrija


In the West Village, in bridge-and-tunnel central, I passed a group of three guys, all wearing identical short-sleeved, button-down collared shirts — made of mesh. As I passed, one shouted “Schwing!” — Rachel


I was sitting at a bar a few Saturdays ago, when a man came up behind me and asked me to dance. After I politely declined the offer, he attempted to keep my attention by asking if I'd like to see a magic trick. He then pulled two coins out of his pocket, waved his hands around, and somehow made them disappear before asking me to dance again. I appreciated the perseverance but magic tricks are a dealbreaker. — Caroline


A guy once said to my (female) friend, “My friend is hung like an elephant — I know because I've jerked him off. Just saying, in case you're interested." — Rachel


When I lived in Argentina, a woman bumped into me — causing me to spill my drink all over my shirt — and then admitted she’d done it on purpose to start a conversation. Her rationale was that it was an open-bar party, so I could get another one if I wanted. I was, however, still covered in whiskey. — Dan


I once drove from Philadelphia to Yale, snuck into the dorms, went to an outside balcony, and put a box of mac and cheese on a fishing pole and dangled it through the window of a girl I liked. She was pretty weirded out, I think. We actually ended up dating, but not ‘til years later. — Charlie


In college, an upperclassman tricked me into attending his fraternity formal as his date. He pretended he was inviting me to a fancy party on the Circle Line Cruise around Chicago and that all my friends could come. My friends could not come. He was a liar and it was a trap-date. I vomited on his shoes that night though, so in the end, the joke was on him. — Megan


I had an older woman patient in the emergency room, and was in the middle of explaining her treatment plan to her adult son — when he handed me a piece of paper with his phone number on it. I left it stapled to the front of her chart. Don’t try to pick someone up when your mother is sick in the ER. — Teri


A few weeks ago, this guy approached me and said, "Damn girl, you make my dick swell up like a pregnant lady's ankles." It didn't work out so well for him. — Jamay


I was on a photo shoot for work at a local restaurant. While I was talking to the manager, he told me he knew me from somewhere. After asking me where I went to school, what bars I frequent, etc., he then said, "I know! I'm pretty sure I had a dream about you the other night." — Katrina


‎"Oh, you're so tiny and cute! I just wanna take you home and lock you up in a cupboard!" — Shannon