Swiping (Right) In The 6

Update (February 13, 4:45 p.m.): Through a rep, OB OBrien said the Tinder account described below did not belong to him.

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Here’s a story I heard once at a party. On a typically nice day, a twentysomething woman was lounging around sifting through profiles on Tinder when, from the sea of faces, emerged OB OBrien. His About Me read: “Can I hit it with my OVO Goose on?” It was too good a find to swipe left, and so a match was made. (A request for comment from OBrien, sent through Facebook, was not returned.)

A clarifier for the uninitiated: OB OBrien has been best know as an affiliate of Drake’s OVO crew—you know, the one with the ginger facial hair. He’s the guy who comically fluffs his beard with a pick and speaks directly into a woman’s breasts while trying to pick her up in the video for “Started From the Bottom.”

But what was OB doing swiping in the six?

It seems for the same reason as everyone else: to hook up. Famous people use Tinder in every major city. (There’s even a dating site similar to Tinder that is specifically for the rich called Luxy; to sign up you have to provide your income and a list of preferred luxury brands.) But in Toronto, and other mid-sized metropolitan areas where social scenes are compartmentalized, people are removed by just one or two degrees of separation. Men with more localized notoriety have begun to use Tinder and analogous dating apps to set up meetings with the same women they meet in person, often at the club or a nouveaux-dingy neighborhood watering hole. But why? It's because dating apps help men skip the awkward step of waiting for a woman to assess their fuckability face-to-face.

In this way, dating apps now function as sort of a litmus test for emotional consent and approachability. Because here’s the thing: people with inflated social status are on the same emotional ground as the rest of us. They’re afraid of rejection, too (and, perhaps, of coming across as creepy in a time when misogyny is becoming less and less tolerable and more women are outing assailants of sexual assault). Even in “Hotline Bling,” Drake hints at the unease of a woman moving on and rejecting him. These days, all I do is/ Wonder if you bendin' over backwards for someone else/ Wonder if you're rollin' up a backwoods for someone else/ Doing things I taught you, gettin' nasty for someone else, the Toronto rap star sings.

Given this fear of repudiation, it makes sense that people joke about toilet Tindering or that the internet is memeifying de rigueur customs like Netflix and chill. Untold numbers of people suffer from sometimes-debilitating levels of social awkwardness in scenarios that aren’t heavily premeditated. As a result, we are finding it more difficult to improvise in social situations.

Jen Stith is vice president of brand development and communications for Bumble, a dating app that works just like Tinder—except women make the first move. With dating apps, she says, “the possibility of rejection is eliminated.” If you don’t match with someone, it’s easy to shift the blame to distance, age, or other settings not in alignment and just keep swiping.

At this point, achieving success in online dating is practically science. According to researchers at Barts and the London School of Medicine and the University of North Texas, what makes a profile appealing is fairly simple: make sure your profile is “close to reality”; post smiling photos, include a 70:30 ratio of information about yourself versus what you’re looking for, and, if you’re a woman, wearing red—apparently—helps.

For IRL interactions there’s no such formula, even for celebrities. Khloé Kardashian is on OKCupid, and Leonardo Dicaprio and Hilary Duff have reportedly been spotted on Tinder. While swiping through Bumble one day, I came across Tim Warmels, the bachelor from the most recent season of The Bachelor Canada. This is a man who had 25 women quit their jobs, stock up on ball gowns, and fight each other for his love over the course of several months. And yet here he was, scrolling through strangers like the rest of us.

I’ve been single since August, and in that time I’ve “dated” an “actor-slash-comedian,” the manager of an aspirant rapper, and a few men with perpetually perfect hair and impossibly maintained sneakers who throw monthly parties at clubs. These are the type of men who go out most nights of the week and are often the center of attention. In theory, they shouldn’t have issues meeting someone.

Prior to matching on Tinder, I’d already eyed most of these guys from across the room, sweaty bodies dancing in and out of my line of sight. One of them—let’s call him Jay—pretended we didn’t know each other even though we had spoken on OkCupid in the past and frequented the same events. Later he referenced seeing me at the exact party where we had first eye-fucked a year earlier. Another kept talking about how odd it was that he’d never seen me out despite having so many mutual friends. What he didn’t know was that I already knew his name since he was friends with my ex.

Recently, I was texting with the owner of a well-known bar in Toronto. We had just matched on Tinder, even though we had crossed paths before (I interviewed him years ago when the bar first opened). When I gave him my number, he realized he already had it. We could have asked each other out at any time over the last, oh, 1,200 or so days, but instead we waited until we were sure it was a low-risk proposition.

For him, this dynamic is common. He told me that he usually goes online only to end up scheduling drinks with women he’s met in person. I asked why he bothers using Tinder when there is a constant parade of women storming his workplace.

“It’s kind of a cheat, I guess? You find out someone is single and if they have the slightest interest in you, you match,” he said. “All without really taking the risk of blindly asking someone out.”

My friend K, who lives in Montreal, told me none of this surprises her.

“You know how we go out to a club and we’re like ‘Ew, don’t talk to me?’” she says. “On Tinder, you’re on even ground. I think people have the same insecurities, whether they’re well-known or not.”

One of her exes is a well-regarded media mogul who regularly frequents parties, the type of guy who already knows (and has had sex with) every woman in town. Despite his success meeting women offline, she tells me that he collects women as a security blanket, using Tinder to make sure he doesn’t miss out on potential partners.

“Even if he has the hottest woman on his arm,” K tells me, “he wants three.”

Hookup apps, Amy Galland says, deflate our dating angst considerably. Galland created two emoji-based apps—Plume and flirtyQWERTY—which were designed to foster more intimacy between people as they text. If our fear of rejection leads us to the point where we spend more time online and less time pursuing people in person, she says, we may fall into a web of building connections that seem stronger than they actually are.

“Sexting is the new first base,” Galland says. “But one of the downsides is that with some people, it ends up taking the place of a face-to-face interaction, creating a false sense of intimacy.”

She wonders whether the anonymity of the initial online connection is an added plus for local celebrities, “because no one at the club, bar, park, et cetera, could record—and post on social media—what is an inherently awkward and oftentimes clumsy interaction.”

Yet, despite the modern ways in which we search for love (or sex!), one cardinal rule remains true of hookup culture: to be successful you must, to some extent, feign noninterest. After all, no one wants to be caught catching feelings too early; it’s embarrassing. And knowing Drake—or even being Drake—doesn’t make one immune to this rule.

The woman who told me the story about matching with OB OBrien ended up writing him a tailor-made joke, hoping it might pique his interest: “Haven’t I seen you at the Shoppers [Drug Mart] on Dupont?” she wrote, referring to his memorable appearance in the "Started" video.

The OB account, she said, never responded.