“The Tinder Generation
Alana Hope Levinson

My Bisexual Date Told Me How He Went On Tinder, Office-Banged a Trans Woman, And Is Down For Anything

#Generation Tinder

My phone buzzed with the message: Jim is here for you at the front desk. The phone was on my desk, because I’d invited a man I met on Tinder to come to my office for lunch, which I acknowledge is all kinds of crazy and could end in all sorts of epically career-bombing ways. But only the brave and spontaneous prevail in the wilds of Tinder, so when a late-40ish bear-looking man accepted my invite within minutes of swiping right on his face — no further questions asked on his end — I rolled with it.

Let’s back up for a second. This was as pure of an experiment one could get on Tinder — I loaded a pic, swiped right on every single male and female (I told the app to show me both), and immediately sent all those who matched with me an identical follow-up message: “I’m a journalist writing about the ways people use tinder. Would you be up for a chat this week?”

I didn’t have the guts to get on this app when I was actually single — being judged on my physical attributes alone seemed terrifying. I felt like I was saying yes to first-date sex just by downloading the app at all… a weird kind of pressure to put on an already stressful ritual. But when I was granted a little distance, I swiped without fear.

Apparently this guy had been, too. Ten minutes later, and boom, my first response: “yeah, I’m in! names changed to protect the guilty, right?”

So Jim* — *name changed to protect the guilty — arrived. He was far from the manicured, sleek seals of Manhattan men in the Vanity Fair article blowing up last week, the type who are apparently destroying romance for all and making Manhattan women lower any expectation of romance or decorum on the path to getting laid. No, Jim would likely not have made the cut for the Vanity Fair article, but like it or not, aspirational glossies, he’s a part of Generation Tinder, too.

The optics: Jim showed up a bit sweaty, teardrop dollops of sweat soaking through his blue button-up shirt and resting on his brow. In person, he was less bear-like than in his pic — he had a rather weathered, sunburned complexion, and aviator sunglasses pushing back his blonde hair in a sort of Florida White Guy way. He set his bluetooth headgear and his giant Starbucks cold brew down by his plate, (“my afternoon drink,” explaining some of his frenetic energy), and as matter or orientation, looked around the cafeteria and asked so what does this company do?

The backstory: Jim had just moved to San Francisco from a mid-sized town in the Midwest, where he’d lived his whole life, had an amicable divorce four years ago, and has one teen daughter. His story spiced up from there: he was bisexual, and had come to San Francisco to open a new business venture, and was currently crashing in an Airbnb in Oakland. He wasn’t one to approach potential mates in public — sort of an unexpected admission from such a gregarious guy.

“I have horrible approach anxiety. I just don’t have strong game.” Back in the Midwest, Jim had hooked up with men from Craigslist, but found Grindr to be “too hardcore, dare I say slutty.” But he enjoyed a wider range of relationships with women, and so, post-divorce, tried Tinder. No luck back in the Midwest — only chatting. “If I want a text buddy, I have already have those, thank you very much. This for actual tangibility.” San Francisco was a different scene, a “target-rich environment,” as he put it. In just one month of swiping, he’d messaged with 15 people, and gone out with two.

“I’m totally open to the cadence the evening takes…It could be a nice dinner and drinks. It could be a tawdry dalliance…I’m not precluding anything, I don’t do that in my regular life, so why would I do that on Tinder? When women on there say I’m not looking for a hookup, I say how do you know? If Brad Pitt is on there and says yes, swipes right, would you not hook up with Brad Pitt? I bet you would.”

His Tinder pinged — Destiny* called. (Name is changed for anonymity, but it’s in the ballpark.) He showed me a photo — “she’s super hot,” he said, needlessly — of a dewy skinned, model-beautiful Thai woman in her early-30's in a maxi sundress, looking coyly over her shoulder back at the camera in a casino. No doubt, Destiny was hot. Jim plunged ahead with his typical opener:

This was going fricking great. “This was my chance to go out with a beautiful woman,” Jim explained, enthusiastically.

Jim soon found himself knocking back Anchor Steams served in a icy bucket with her at a cheesy Financial District wine bar that few locals would never step foot in. In the course of the date she revealed she was a masseuse at a massage parlor. He figured out she was transgender. “I’m like, the best of both worlds,” he told me. Destiny ordered a second bucket of Anchor Steams. Things were getting fuzzy.

Jim quickly did the math. The Airbnb was across the bridge, an expensive Uber away. But his new office was in shooting distance. Uber was hailed, and “We ended down at my office, getting rather naked and having some fun.”

So, a success in your book? “I would think so.”

In fact it was so much fun, they executed the exact same routine the next week — copious drinks, dinner at Burger Bar, “conversation not flowing as much,” Ubering to an office shag. The texts sort of fell off after that — a mutually understood two-night stand. The whole affair seemed to feed into his newcomer’s euphoria that San Francisco was a city full of possibility, his true fit. “I’m trying to find out how everyone lives.” And Tinder is part of that.

“I’ll keep swiping left and right for awhile.”

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