DATING ON BAY: Rules of Engagement
An outsider goes undercover in Toronto’s financial district and maneuvers her way through Bay Street’s complex dating landscape.
By Allison Withers
I don’t work on Bay Street. Not even close. Educated at a crunchy liberal arts college, my formative years were fueled by philosophy, literature and the heady concept of “knowledge for its own sake.” At graduation, I had little direction beyond hoping to travel before diving into the “real world.” (Panic about the lack of employment opportunities for a mid-recession arts graduate set in later.)
Needless to say, though most of my friends and I have settled onto respective career paths, we’re not the folks clocking 14-hour days in the high-rise towers dotting the downtown expanse known as “Bay Street.”
And, unsurprisingly, my dating repertoire contains nary a finance professional or corporate lawyer, comprised rather of out-of-work artists, academics and hirsute non-profit types.
While a modest bank account has, historically, been the key to my heart, I’d be lying if I said I wasn’t a bit tired of the flakiness or instability that is sometimes part and parcel of dating this type of “alternative” guy. Basically, I was curious to explore what the Bay Street dating scene is all about.
A veritable outsider, I set forth collecting anecdotes and observations from professionals who work in the area, and even undertook a foray into Bay Street nightlife. Here’s what I took away:
No one has time to date. My friend *Anne, in her late twenties and an employee at a large, downtown consulting firm, agreed to devote the better part of a Friday night to acting as my Bay Street spirit guide.
She instructed me to meet her at Reds Wine Tavern (77 Adelaide St. W.) at six p.m., patiently fielding my flurry of texts about what to wear. “What should I be going for?” I inquired, knowing my failsafe uniform of skinny jeans and a t-shirt (perfect for the divey West end bars I usually frequent) wouldn’t do. “Corporate? Slutty corporate?”
I opted for an approximation of the latter, but given the five feet of slush outside, forgave myself for wearing bulky winter boots. Upon arrival, I realized this had been a mistake. The bar was full of people wearing crisp power suits, the women elegant in heels and designer footwear. I was not on Ossington anymore. Namely, the floors weren’t covered in a mysterious film and anemic-looking hipsters slouching over pints of Craft beer were nowhere in sight.
I found Anne at the bar, gin and soda in hand. “I just came off a week working 15-hour days,” she said. “This place isn’t really my scene, but after a week like this it’s really nice to come to a bar around the corner from my office and have a drink.”
Anne, who is single, confessed, “I don’t have time to meet anyone.”
The sentiment was widespread among the Bay Streeters I interviewed.
Tia, a 27-year-old corporate lawyer, told me she believes extreme busyness is the reason so many Bay Street-types use dating applications like Tinder.
“When you’re leaving work at nine or 10 every night, it’s really hard to meet someone naturally…Tinder is easy to use, most people have iPhones and it [matches people] by area, so you can meet other people working downtown.”
Not only is it hard to meet someone, she explained, long and erratic work hours make it tough to even keep a first date.
“I’ve had to cancel dates last minute because I’ve been assigned work at five o’clock the day I’m supposed to go out with someone for the first time, and the opportunity to meet them again doesn’t come up again. People outside of Bay Street, especially, often can’t comprehend how late and unpredictable work can be. They think you’re blowing them off,” Tia added.
When, earlier this year, she dated an investment banker, she assumed some of these issues would be alleviated. Instead, it was virtually impossible for the two to find time to see each other.
“Work was always on his mind. He was very intense and had trouble finding a work-life balance. You’d think, since we both worked in the financial district, which is pretty small, it would be relatively easy to meet for coffee or lunch in one of the downtown food courts. But this guy couldn’t even commit to a 40-minute lunch.”
They broke up after two months.
In some ways, Tia mused, dating someone “off Bay Street” is easier, because the odd night she can leave work at five or six, the other person is likelier to be free and not staying at his office until midnight.
Adil, 31, works for an infrastructure finance group in the heart of the financial district. He said his fellow finance professionals often fall into two categories where dating is concerned: those who have been in long-term relationships since university, and those who date online and go out on weekends looking for a “short-term hook-up.”
“The ultimate thing is people don’t have time to date. If you’re very driven about work, as most people on Bay Street are, it’s hard to find someone to put up with that,” he said. “If you’ve already found someone who’s used to that, that’s advantageous, though sometimes I wonder if those people in relationships are genuinely interested in their partners, or it’s more that it’s hard to find someone who accepts the long hours.”
Bay Streeters are aggressive. At Reds, we scoped out the men scattered about the bar. Anne indicated a posse of young lawyers mingling in the corner with a swift jerk of her head and the qualification, “Wedding rings.” Apparently, the lawyers get snatched up early.
An hour later, no one had approached us.
“I thought Bay Streeters were supposed to be forward,” I complained.
“Earls,” she replied briskly.
I consented, having heard that the popular restaurant and bar chain’s King St. and University Ave. location was a somewhat notorious pick-up spot among the Bay Street set.
Colleen, a credit analyst for Scotiabank, had told me about the time she and a girlfriend were having dinner there and, in the middle of their appetizers, three men had sat down with them, uninvited.
“They started going on about how this one was the vice president of this, and another one owned X company, and I’m thinking, ‘that’s great for you, but I totally don’t give a shit. I’m in the middle of eating food,’” she recounted.
She finds men in that world overly confident in a way that’s off-putting.
“It makes sense that competitive people are the ones who are able to work in this type of environment, and then that comes out in everything they do in their lives, including dating. This isn’t to say that everyone is like this, but, it does seem to be part of the culture that men here feel like they can do whatever they want.”
She added, “Perhaps many of the women are like that as well, but at the end of the day, it’s still a male-dominated industry.”
Tia finds dating as a female Bay Streeter hard for different reasons.
“A lot of women, if they meet a banker or lawyer at a big firm, are excited to go on a date with them. But for an extremely career-focused woman, I think it’s more difficult. Men who aren’t of equal or higher career status are afraid of us. They find us intimidating. Like, a teacher probably wouldn’t ask me out.”
At Earls, Anne and I capitalized on the seven-dollar double mojito special and chatted with the bartenders. One told me there’s a fairly wide discrepancy between the bar’s afternoon and nighttime vibes.
“In the day, there are guys in here telling me about their wives and kids, and at night, they’re in here with women who are definitely not their wives.”
Two gentlemen in their forties approached and asked to buy us drinks. We accepted, and talked with them awhile; one showed me photos of his teenaged daughter, a model, on his phone. He later sidled up to Anne, but when she rebuffed him, told us a young lady was on her way to meet him. Indeed, an attractive woman in her twenties showed up shortly after, and the three of them withdrew to a table.
Emboldened, I suggested we chat up two burly guys I was convinced were hockey players (they weren’t). We sat with them and discussed their respective marriages, their sex lives and what they insisted was the sleaziness of the bar’s clientele. I eventually kicked Anne under the table and suggested we go home, to the protestation of the one sitting next to her.
Bay Streeters get a bad rap. My impression of dating on Bay Street, however limited or biased, was, in the end, nothing too revolutionary. By all accounts, Bay Street professionals are exceedingly busy, as are they, generally speaking, more forward than the men I encounter in the city’s so-called hipster joints (though that’s not saying much).
One interesting takeaway, certainly, was that a number of people I spoke to expressed that “non-Bay Streeters” are frustratingly quick to pigeonhole them, particularly after the economic crash of 2008.
“If I’m at a bar hanging with my non-Bay Street friends and I meet a woman and tell her I work in finance, she’ll kind of treat me like I’m the devil,” noted Max, a
credit analyst at a large bank.
It got so bad he stopped telling women what he did altogether, unless sensed the promise of a serious connection.
Adil corroborated: “When I tell a girl what I do, I find myself being conscious of trying not to sound like a Wall Street crook!”
All in all, though I don’t see myself returning to Earls anytime soon, the whole Bay Street scene now feels a lot less foreign to me. And perhaps, with the right banker and the wrong kind of shoes…well, you never know.
*All names have been changed, in order to protect the privacy of those individuals interviewed.
