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10 Stories About Unexpectedly Successful Pickups
"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.
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.
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...)
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.