The Bay Street Tinder Diaries: Dating in the age of the Internet hookup

At 5:30 p.m. on Thursdays, Earls at King and York is roaring. From the surrounding towers, players descend to blow off steam and seal the deal—with clients and that night’s conquest. This is their playground. And Tinder is their Little Black Book

The Bay Street Tinder Diaries: Dating in the age of the Internet hookup
(Image: Dave Gillespie)

Valerie met “The Suit” on Tinder. She called him that because he was the quintessential 30-something Bay Street guy—handsome, wealthy, confident and married to his job in finance. Valerie, like others I interviewed for this story, spoke on the condition that her real name not be used. She’s in her late 20s and also works in finance. She lives in a downtown condo and often travels internationally for work. Like The Suit, she’s an aggressive, high-functioning, time-strapped professional, and she found that men who worked downtown were more likely to share her pragmatic approach to dating. Plus, these guys were close by. Giving Tinder conquests nicknames helps Valerie and her girlfriends keep track of who’s who during their daily debriefs. It’s also part of the fun. There was Miami Vice (drove a white Range Rover and had a slicked-back ’80s hairdo), Bromeo (who bragged about his designer loafers) and Sweater Vest—a nice guy who took her to the AGO and invited her to a friend’s housewarming party, but ultimately, Valerie didn’t feel a spark. Which is important to her. She says a lot of guys she meets approach dating like an investment, and she checks a lot of boxes—she’s smart, career-driven and a knockout, with Barbie-blond hair and Brooke Shields brows. But if the passion isn’t there, she’s quick to cut things off. With The Suit, chemistry was never a problem. Sometimes they did the typical getting-to-know-you activities—going to the movies, cooking dinner at her condo. But often, their meetings were transactional. And the sex was hot.

For Valerie, the advantage of conducting her sex life through her smartphone is that it allows for maximum productivity with minimal effort. With a series of quick clicks and swipes, she can schedule dates with a new guy, sometimes two, every day—mostly coffees, which are a good way to see if the attraction she feels from a photo measures up in person. If a prospect seems promising, she might agree to a future drink. If not, he’s eliminated from the “roster,” which is the term Valerie and her friends use to describe the collection of Tinder guys they are simultaneously messaging or dating. These women are part of a generation reared on Sheryl Sandberg and Marissa Mayer—ambitious, fearless and wildly confident about what they want. They have no time to nurture long-term relationships. The men in their lives are conveniently slotted in for sex—and Tinder is the tool that makes it all happen.

The first time I heard about Tinder was in early 2013, from a friend who works on the trading floors in Toronto. The app didn’t officially launch here until December of that year, but it infiltrated the financial district first, passed along from horny Wall Street bros to their horny Bay Street brethren like a secret fist bump. For those who are unfamiliar with the world’s most popular people connector, here’s a crash course. Tinder was created by a group of 20-something friends working in a start-up incubator in California. It launched on American university campuses in September 2012 and, like Facebook, slowly trickled out into the non-collegiate world. Today it has an estimated 24 million active monthly users, nearly 3 million in Canada, and it’s used primarily by 18- to 34-year-olds. The brilliance of Tinder is its simplicity. It whittles the once-complicated time suck of seeking love online into one explicit question: do you look like someone I might want to have sex with? If the answer is yes, you swipe right. If not, you swipe left, and another possible partner appears on your phone screen. You only get “matched” if the person you expressed interest in reciprocates, which is the second prong in the Tinder success strategy: the absence of rejection, and all of the emotional turmoil and self-loathing that goes with it. So you didn’t get matched, so what? Just keep swiping. Tinder users can evaluate 50 potential partners in the time it might take to have a meaningful in-person interaction with one. It’s an easy fit for a generation that has grown up communicating via text, problem solving with Google, shopping on Amazon, and sharing life’s magical (and not-so-magical) moments through Instagram.

People often use the expression “playing Tinder,” illustrating the extent to which the quest for companionship has become a pastime: they use the app because they’re bored, because they want a quick ego boost, because they can’t get to sleep or because the line at the bank is taking forever. And they use it because smartphones have become a fifth limb. (There’s even a modern malady called nomophobia, which is short for no-mobile-phobia, to describe the deep psychological attachment people have to their phones.) Tinder uses your phone’s location services to allow you to set your “dating radius” as close as one kilometre. That feature was pinched from Grindr, the successful gay hookup app founded on the basic idea that casual sex, like real estate, is all about location. Data collected by students at Indiana University about Tinder shows that young, straight people feel the same way: matches made within one mile of each other are 54 per cent more likely to result in a meetup. That percentage drops by half with every additional mile.

(Image: Photographs by Erin Leydon; Styling by Skye Kelton; Hair and makeup by Nina Farrauto. Location: The Thompson Hotel)
(Images: Erin Leydon; Styling by Skye Kelton; Hair and makeup by Nina Farrauto. Location: The Thompson Hotel)

Tinder is most popular in young, urban hubs—concentrated areas where people live and work and party. In Toronto, this means the downtown core, which over the last decade has become a nexus of shiny towers filled with one-bedroom condos aimed at SINKs and DINKs (single- or double-income, no kids) who walk to work, eat out three meals a day and put in 60-hour work weeks. People in their 20s and 30s make up half of the downtown population. It’s a highly skilled, highly educated group that’s out-earning the rest of Toronto by an increasingly high margin: in 1990, the average person living in the downtown core—between Yonge and Simcoe, and Queen and Front—made $45,623 a year (158 per cent more than the average person in the GTA). By 2012 the average income had more than tripled to $157,909, which shakes out to three and a half times the metropolitan average. Meanwhile, the landscape has evolved to better serve the frenzy of disposable incomes and insatiable appetites, morphing over the past few years from the land of the three-martini power lunch into a no-limits party megaplex—Candyland for the suit and tie set.

The bigger, bolder downtown scene kicked off in early 2011 with the opening of Earls at the corner of King and York. It’s a western import, known for its big burgers and attractive servers, so it’s no surprise that for the first few months, the clientele was made up mostly of young men from Bay Street. While their elders concealed wedding-band tans down the block at Bymark, the next gen swiftly turned the Earls patio into the city’s most reliable destination for debauchery—a stew of booze, boosterism and pheromones. In 2012, the decades-old power lunch institution Reds introduced a more casual revamp, with the goal of attracting this younger clientele. A year later, The Chase and Drake One Fifty opened their doors—the latter tipping its hat to the new neighbourhood by changing the name of its house wine from Starving Artist (as it’s called at the Queen West flagship) to Fat Banker. Last year came Speakeasy 21, a sprawling Prohibition-themed cocktail bar in the Scotia Plaza, and America, the Donald-endorsed ode to gluttony housed on the 31st floor of the Trump Hotel. And before 2015 is out, the Cactus Club Café will open in the prestigious First Canadian Place building. Like Earls, it’s another chain from the west known primarily for its sexy wait staff and showy wine lists. All of these places bill themselves as restaurants, and it’s true that they all serve good food, but culinary merit is beside the point, particularly on Wednesdays and Thursdays (the Bay Street weekend), when they fill up like Irish pubs on St. Paddy’s Day. By 5:15, getting a seat can be impossible, which is why interns are often sent down around 3 p.m. to secure the best real estate. People go to unwind (i.e., get hammered), do business (i.e., get hammered on the company credit card) and socialize (i.e., hook up). That last endeavour has become easier than ever post-Tinder, which is particularly well tailored to a world where efficiency, adrenalin and closing the deal—whether it’s a multimillion-dollar merger or a quick boink in the bathroom—are the unofficial religion. “It’s just insane how drunk these people get,” says one Earls server I spoke with. She has seen people puke on the bar, and says there’s often evidence of sex and drug use in the bathrooms. Earls even has suited bouncers subtly patrolling the lounge floor during the after-work frenzy. Spurning the advances of horny Bay Streeters is all in a day’s work for the servers. “Let’s put it this way,” the server adds. “If I had to choose between dating a professional hockey player and dating someone on Bay Street, I would pick the hockey player.”

About a year after Tinder launched, one of its co-founders, Justin Mateen, gave a controversial interview in which he explained how women “aren’t wired” to enjoy casual sex, and therefore it was wrong to label Tinder as a hookup app. Nearly two years later, it seems clear that Mateen—who stepped down as CMO last fall following allegations of sexual harassment by his former girlfriend and co-founder of the company—was as confused about the core identity of his product as he was about the women who use it.

So-called “female wiring” was the subject of a recent study at the University of Ottawa. Polling more than 500 women about their motivations for intercourse, researchers were able to contradict Mateen’s age-old, gender-specific assumption—that indiscriminate sex is a biological imperative for men, whereas women connect sex and desire with feelings about intimacy, companionship and stability. The data showed that single women have casual relations “because it feels good,” because they are “horny,” and because a hot man is a terrible thing to waste. Heather Armstrong, the human sexuality researcher who headed up the Ottawa study, says she was surprised by the extent to which the physical reasons for casual sex were paramount. “I think a big part of it is that women are feeling more entitled to express themselves sexually, attitudes are changing and it’s not so much of a taboo,” she says. When I ask whether Tinder is the chicken or the egg when it comes to a rise in sexually liberated young women, she says it’s likely both: “These apps have certainly addressed an existing demand, but they have also encouraged the behaviour by making it so normal and easy. People see their friends on apps like Tinder. It just isn’t a big deal.”

A lawyer friend of mine says this applies directly to hooking up on Bay Street. “It was always a meat market, and Tinder has only made that expression more literal.” And that applies to married people, too. “Think about who gets to be wealthy in this world,” says Noel Biderman, the CEO and founder of Ashley Madison, the Toronto-based website for people looking to have sex outside of their relationships. “For the most part, it’s a risk taker. If you’re a risk taker in your business life, you’re more likely to be a risk taker in your personal life.” Over the years, he has learned that there is no greater predictor of infidelity than affluence. People with lots of money become obsessed with the trappings—the houses, the fancy cars, the trips, the toys. Is it any wonder they want the same shiny-new-toy factor in their sex lives? “Nobody has come up with a word for the male mistress yet,” he says, but this unnamed phenomenon (the manstress? The histress?) is a notable new trend from the demographic data that Ashley Madison collects to better understand its customer base. Turns out just as many financially successful women as men approach monogamy with a loosey-goosey attitude.

Of course, people can and do use Tinder to forge more commitment-focused relationships (a spokesperson for the company says they have received thousands of emails with stories of engagements, marriages and even a few Tinder babies). They also use it to find platonic friends in new cities, as well as for professional networking purposes. Still, none of these functions is at the root of Tinder’s meteoric rise. The app took off because rather than stigmatizing hookup culture, it gives users permission to revel in it. Where previous online dating services have fundamentally been about finding The One, or at least branded as such, Tinder says, Go ahead and make superficial judgments, keep a few partners on the go, be casual, have fun. It says this to both genders—the only difference is that for women, the message is relatively new.

Stacey is a doe-eyed lawyer in her late 20s. she works 80-plus hours a week. It’s possible she’ll get to the whole marriage and family thing—eventually. For now she says Tinder is ideal in the work-centric, oat-sowing, sorta-single stage that so many young, career-driven women currently find themselves in. “Women of my generation have been told our whole lives, you can have it all,” she says. “A rewarding relationship, a successful career, children. The reality is that I haven’t seen many relationships where that’s the case. When a couple decides to have children, it’s almost always the woman who takes herself out of the workforce or asks for a less demanding role. And her career suffers for it.” Stacey recently hooked up with an ex she compares to the kale salad at Gusto. (“It’s good, you know what you’re getting, but, you know, nothing mind-blowing.”) Before him there was the guy she and her friends called Runway, a reference to his career as a model. They met through Tinder, and while Runway was nice to look at and okay in bed, eventually he overstayed his welcome: “He would be hanging around at my apartment, and I was always thinking, can you go now? I have to go to work.” Stacey admits that Tinder makes her less considerate toward the men she’s dating. “You invest so little that you can literally be on a date and get up to go to the bathroom and leave.” Freed from the tyranny of forever, these women collect different men to suit different occasions: there’s the guy who makes you breakfast, the guy who gives great foot massages, the guy who can get you into all the best restaurants and the guy who will show up at your condo even if you message at 3 a.m. to “cuddle.” Stacey will often go on Tinder when she wants a quick ego boost or a reminder of how many men are out there. The ritual has resulted in a condition she and her girlfriends identify as dating ADHD. “The problem with social media is that there are so many options. You get into a fight with a guy you’re seeing, so you just swipe, swipe, swipe.”

The latest data shows that women are pickier than men. They swipe left (say no) three times more often than men do (46 per cent of the time versus 14). All Tinder users have to go on is a first name, age, a cheeky bio line and a few photos, and yet they assess their potential matches in a matter of seconds. The women I spoke to have developed a visual vocabulary of red flags. A guy who doesn’t post his height is probably 5 foot 7 or shorter; if he wears a hat, he’s got the hairline of a pre-Regenix Matthew McConaughey. Last year, “tiger selfies” (yes, meaning a man snapped side by side with a tiger) were Tinder’s most inexplicable trend. The bizarre practice was so rampant in New York that Governor Andrew Cuomo signed a bill banning it. Here in Toronto, tiger selfies are still legal, though a surefire sign of douchebaggery. Other popular if questionable Tinder props include sports cars (big ego, small penis) and cats (kind but clingy). Sunglasses are a category unto themselves: big sunglasses equal bad face, Oakleys equal an address in the burbs, Kanye shutter-style shades equal a Jersey Shore–style partier. A guy who posts a photo with a bunch of other guys is probably hoping you’ll confuse him with one of his better-looking friends, while a guy who posts zero photos with friends probably doesn’t have any. Tinder has turned men into a commodity, and Stacey and her female friends evaluate potential partners like seasoned market analysts discussing pork belly futures.

Critics of tinder say it’s killing romance. But many of the women I spoke to believe it’s slowly doing away with any residual stigma that society still attaches to casual sex. “My dad thinks I’m addicted to the chase,” says Valerie. “He’s probably right. But I’m having fun, so why can’t I be as superficial as the men? I remember when I was in high school and we’d say things like, ‘Oh my god, that girl is such a slut.’ I haven’t used that word in years. If one of my girlfriends is having tons of sex, it’s like, hell yeah!”

Valerie and The Suit would often spontaneously hook up in the middle of the day for a quickie. “We were always searching for the best washrooms to do it in,” she says. “We would message each other about where to meet. I would always go in first and then he would come in.” It was hot (as most I-want-you-so-bad-we-have-to-do-it-in-the-PATH trysts tend to be). Sometimes they wouldn’t exchange a single word before returning to their respective office towers. A couple of Valerie’s colleagues knew about her escapades and would tease her when she arrived back at work with tousled hair and flushed cheeks.

But the steamy romance with The Suit ended when Valerie discovered, via Facebook, that he was in a long-term relationship. She was angry and disappointed that he cheated, but thanks to Tinder, there were plenty of new guys to add to the roster. A couple of months later she ended up on the quintessential disaster date with a guy she matched with and agreed to meet after chatting a few times on Skype. When she arrived at the bar after work, he was already hammered. Since he had his car, Valerie offered to drive him home, but she wanted to stop at her place to change out of her work clothes. When they got inside, he wouldn’t leave. Eventually Valerie turned in and left him on the couch. He spent the night drinking his way through her liquor cabinet and started throwing up around 5 a.m. Valerie insisted it was time to go. She gave him a lift home, and he cried the entire way. Later, on her way to meet her girlfriends, she checked her phone and saw he had been texting her from the couch while she was sleeping.

“I’m so happy we met.”

“I feel like we’re really connecting.”

On weekends, Valerie spends time with her female friends: they work out, gab over coffee, visit a hot new restaurant or catch an art show. It’s the sort of stuff people do with a significant other, but for these women, the most important people in their lives are each other. “I only have so many social hours in the week, so why would I want to spend that time with some random guy?” Down the road they might be interested in the kinds of traditional relationships their parents had, but for now, life is work, eggs can be frozen, friendships are fulfilling, and sex is just a swipe away.


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