Love & Sex

10 Stories About Unexpectedly Successful Pickups

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"The cop asked for my info. When I leaned in to get it…"

I was at a bookstore, having trouble finding The Ethical Slut among the shelves. I had to ask for help from a young man who found the book in the online system and then led me to the shelf where it was located. Upon looking further at the title, he said it would be an interesting read and maybe he would check it out. I said he should, as it was supposed to shed an interesting light on healthy, non-monogamous relationships. He said the toughest part would be to find someone who would agree to such a thing. Where would he go about looking?

I laughed and, not really thinking, answered, "Bookstores." It took a second for him to register what I had said, and then he asked if he could have my number.

— Sonya

I was at dinner with my dad shortly after my parents divorced. I hadn't been going out much or trying to date at the time as a result of the fallout from the separation. Our (very cute) waitress was clearly hitting on me, so I wrote my name, phone number and "Just in case…" on the receipt. She called the next day, and we went on two dates. The first was a lunch date to a vegan restaurant; it happens to be the best first date I've been on to this day. The next night we went to see a movie. Afterwards we parted ways and I never saw her again. I felt like the man when my pickup method actually worked, but also learned the valuable lesson that movie dates that early on are fucking awkward.

— Graham

My greatest pickup happened when I was on my way for coffee the morning after a night of partying. I got pulled over, and the cop asked for my info. When I leaned to get it from the glove box, he commented on the tattoo on my side. I thought he was a little brazen. He went back to his car, and when he returned, he was nice enough to let me off with a warning.

I went in for coffee, and when I came out, he was still in the parking lot. So I decided to be bold. I pulled up next to him and asked what he was doing that night. He had to work, but he gave me his number. A week later, we hooked up — nothing like the sound of a cop's belt hitting the floor!


My most successful pickup happened at a Halloween party in Boston. I was dressed up as a gay cowboy, as had been my Halloween habit for the past few years; my friend accompanied me as my mustachioed lover. We shmoozed around for a while, talking in bad Southern accents and sipping whiskeys. Across the room, a girl came into my field of vision, wearing a sparkly silver dress, blonde wig, and a bloody nose. "I'm a coke-whore," she said. I laughed and asked if she meant "on Halloween" or "in general." She gave me a wry grin and winked.

As the party grew bigger, I led her outside for a cigarette, and we ended up alone together on the porch. She asked me about my job, and I told her I was a cowboy. "Brand me!" she said. I took out a sharpie, took her arm, wrote down my number, and signed my name. She called me. (Turns out she was kind of a coke whore, though…)

— Jeremy

I was at an all-too-popular speakeasy, getting a drink with my best friend's girlfriend and trying to chat up the waitress. The second part wasn't working very well: aside from having to clear the hurdle of the traditional waitress/drunk-sleazeball relationship, I probably just seemed like an asshole who was ignoring his date. (Even though she wasn't actually my date.) Safe to say I didn't get very far, but I did discover that the waitress was a jazz singer on the side, and that was hot.

A few months later I went back with friends, about three drinks deeper than I'd been on the previous visit. I recognized the waitress, but she didn't recognize me. Taking advantage of that, I chatted her up a second time, and claimed to have seen (and been stunned by) one of her performances at that very speakeasy. She complained that her manager hadn't let her sing in a months.

In outrage, I burst into the back office, interrupting a dinner meeting between the manager and five of his colleagues, and told him off for letting her tremendous talent go to waste. I told him I'd never been touched by another performance there or anywhere else the way I had been by hers. Flustered, he agreed to put her on the following Sunday. When I left the office, the slackjawed and breathless waitress said, "Oh my God, that was crazy! And really nice!" I said, "Yeah, I'm crazy. And really nice." Needless to say, she remembered me that time.

— Garrett

I had just moved back to New York from studying in France/dramatically dipping out of a terrible relationship by moving to another country. I was ready for action and everything seemed new and exciting. Someone rang the doorbell; I assumed it was the delivery people bringing me a large piece of furniture, but as I went to answer the door, I locked myself out of my new apartment. My new roommate was out of town, and my phone was inside.

One of the delivery guys was very handsome, so I felt extra-stupid. But we all decided, as people in crisis in New York often do, to work together to fix it. The only real solution would be to break into my apartment through my roommate's window, which we might be able jimmy open by way of her air conditioner. A neighbor came out and used the handle of a broom to force open the window. Once the window was slightly open, Handsome Delivery Person leapt through the narrow opening with astonishing grace, and everything was back to normalish. I told him I never expected anybody with a beard to be so agile. We dated for four months.


I was at Applebee's with two friends (a couple) and their friend Terry. Terry was an asshole who, for some reason, always acted like we were in competition with each other in everything from charming girls to who was better friends with our mutual acquaintances. Our waitress was Anne, an adorable, nerdy girl with an easy laugh and a shy smile. I started getting flirty, for my own amusement mostly, but also to show up Terry.

There are few things I dislike more than lemon in my water — wet socks and soggy bread among them — but every restaurant seems to believe that everybody enjoys it. So I specifically asked for no lemon, making a cartoonishly big deal of it. Anne giggled.

A few minutes later, she set a cup in front of me. Floating there was a tiny plastic sword speared through every kind of fruit they had in the kitchen, including lemon. I stared at it, confused. Anne laughed and took the cup away, saying, "Sorry, I thought it was funny."

When we paid the check, I wrote my phone number on it, and underneath wrote: "Connor (the cute one)." Not more than fifteen minutes later, she texted me and asked with a smiley, "So, Connor, were you no-lemon-in-my-water guy?"

Take that, Terry. You jerk.

Connor Thomas Cleary

Back when my boyfriend of five years was just some guy I liked, the following happened: one night, I dreamed that I was hanging out with him, and I whispered something in his ear. Then he gave me a piggyback ride, and it made me so happy.

A few days later I saw him at a party, and I whispered in his ear that I'd dreamed about him giving me a piggyback ride. He drunkenly offered to give me the ride I'd been dreaming of, so I hopped on his back and rode him home. Subtle, right? It sounds sort of stupid now, but at the time I thought it was pretty cool that my dream told me how to get my man when I couldn't figure it out on my own. Just tell him you want to ride him!

— "Katniss"

In the middle of a regrettable Hunter S. Thompson phase that consisted largely of eating whatever drugs I could get my hands on and wandering around trying to feel profound, I had taken some mescaline and was riding out the end of what proved to be a paranoid, disappointing experience in an abandoned laundry, staring at the mesmerizing swirl of the machines. A tall, prim looking girl with glasses came in to do laundry and ignored me for a few minutes, before finally asking me, "Are you still using that?" Apparently the machine in front of me had stopped, and I was still staring intently at it. Startled, I responded, "Oh, I'm sorry, I'm on mescaline." It was an honest response, but it's also a line from The Royal Tenenbaums, and she responded with "I'm sorry, did you just say you're on mescaline?"

"Indeed I did," I said, finally catching on. "Very much so."

"That's so weird," she answered. "I was just about to watch that movie. Do you mind?" We watched it on her laptop while she finished her laundry. Afterwards, I helped her bring her laundry to her room, and she asked for my number.

— Alex

I was eighteen, I didn't speak Italian, and I was in Venice, watching the sunset and walking towards the dirty waterfront. A man in a naval uniform was sitting on a speedboat near the dock. Face-wise, he looked like a cross between Eugene Levy and a large earthworm.

"Want to get on the boat?" he asked.

I hadn't spoken to anyone in about a week. I lived in a lonely stone hostel and worked for a poet who preferred silence.

I climbed on.

Together we sped through blue-black waters, circling the old, sinking island. The stars came out, and he tried to entice me. "You're so young and I'm so old," he said. "Yet here we are, falling in love." I resisted. He pulled the boat into a dock and told me that he had brain cancer. He started crying. He stopped the boat and bent his head towards me, looking for sanctuary, nestling his nose between my breasts. His tears dripped down to my navel, inducing a strong flight instinct.

I wrote my email address down on a piece of paper and gave it to him, along with a sympathy kiss. Six months later I got a message:

I am the italian navy officer you met in venice. I would have told you one thing that last night, but pride and tact gave me no chance: you were, still are, terribilmente sensuale. A childish face and the body of a woman. The right attitude toward living and writing. I think of you when I seat on that bench, in piazza Santa Maria Formosa.

— Jia


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