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The Last Time I Went On a Date With Someone I Met IRL

Before Tinder, Bumble and Grindr, there was “real life.” In that treacherous world, swiping right meant introducing yourself to a stranger with the hope of striking up a conversation. It was cruel and often disheartening, in part because you couldn’t determine a mutual physical attraction while sitting on the toilet. But alas, even in today’s swipe or be swiped world, some people are still braving those awkward, IRL introductions. At least that’s what we found when we asked a bunch of guys about the last time they went on a date with someone they met in real life.

Diego, 24

A friend of mine convinced me to go with him to a photography exhibit. He had to convince me because I’d just gotten back from a 30-mile bike ride and my body felt like jello. At the exhibit we ran into a girl that we’d known from high school. I didn’t know it then but the whole thing was a setup by my friend, who thought we’d make a nice pair. I sensed an immediate connection but I didn’t have the balls to ask her out that day. Instead, I texted my friend and asked him for her number. We ended up dating for some months and it was really great until she ate my heart for breakfast and married a different guy a few months after we broke up.

Brody, 26

About three years ago, there was this girl I met in college, whom I’d always had a bit of a crush on. I was creeping her Facebook profile and she was looking good, so I fired up the classic “Hey Stranger” message and she eventually agreed to grab drinks with me. Her relationship status was listed as “single” so I figured I’d be in for a fun night. After about 30 minutes of conversation she told me she was hooking up with one of our old professors, who was at least 20 years our senior. They’re now Facebook-official.

Ryan, 27

The last time I went on a date with someone I met in real life I had one of the greatest, most uncomfortable conversations of my life. It started off with the waitress asking us if we were brother and sister. My date then proceeded to order the worst yet most expensive bottle of wine on the menu. At the end of the night, she said, “This was fun, let’s do it again sometime… as friends.” I haven’t gone on a date with someone I met in real life since.

Brian, 38

I was steaming across the Mediterranean Sea aboard the Celebrity Equinox, an Atlantis gay cruise ship I was hired to write about. My date, Andrew, drank sherry and sounded like Winston Churchill. Over legs of lamb in the Silhouette dining room we traded stories about our respective youth. His was spent at a famous boarding school attended by royals and Eddie Redmayne. I flippantly asked if that was where the term fagging originated, the practice of younger pupils forced to act as personal servants to the most senior boys. I regretted the question immediately. Andrew’s lip quivered as he recounted systematic sexual abuse — from older students and younger faculty alike — both of which he described as being “just part of the experience.” Unfortunately I couldn’t pivot the conversation quickly enough to salvage the date, which proved to be our first and only.

Joe, 28

The last time I went on a date with someone I met in real life, it was with a guy I met at the Whole Foods in West Hollywood. I was searching through the peaches when we accidentally met eyes. I simply couldn’t withstand, not for a second, accidental intimacy with a man this attractive. So I carried on, not taking my eyes off the floor until I reached the safety of the store’s aisles.

But after I paid and walked out, I passed by right in front of him. His phone conversation ends abruptly. “Um, excuse me,” he says. I turn around, unsure. “This is really awkward, sorry, but um — .” He smiles. “I just had to let you know that I think you’re beautiful.”

He helped me walk home with my grocers, we chatted, I invited him in and we had sex right then and there. It was so disarming that someone was expressing interest in such an outward way, I never stopped to think about this person’s kindness or interest in me. I felt like I needed to repay the interest then and there. We’ve maintained a texting, hook-up relationship since then. I think I’ll see him tomorrow.