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Michael Liebrock, left, and Andrew Dale both struggle with Bay Street's macho culture. 'It's not necessarily homophobia explicitly, but it’s this prototype of what a dealmaker looks like,' Dale says.

Kevin Van Paassen/The Globe and Mail

Talking about strip clubs just one gin martini into your very first meeting is, by many standards, a bold move. Not so on Bay Street.

In April I met some corporate lawyers at Reds for after-work drinks, and not even an hour into our conversation one of them made comments about the rippers. It was a casual reference, nothing too pushy, but the message was clear: They assumed I was straight, and this was a good way to make a connection. To them, it's the norm for Thursday nights to end at these establishments.

The lawyer miscalculated. I'm gay. But instead of embarrassing him I played along. I've been to enough strip clubs with buddies and former colleagues that I know how to sound interested. Sometimes you just smile and laugh, other times you simply ask if they went for a 'dance' and move on.

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They didn't mean to be rude, and I actually didn't mind much, but it was a sudden reminder that Bay Street hasn't fully evolved. Before joining The Globe and Mail in 2010, I worked in both investment banking and bond trading, where alpha males, many of whom work on little sleep because they are either grinding away at the office or are hopped up on adrenalin, dominate office culture.

I've seen a call girl hired to wish the head trader 'happy birthday' at the office, watched people fart in each other's faces like little boys, and even had a friend blasted because he sent out an internal e-mail that didn't list the male recipients in order of seniority in the 'to' field. Talk about ego.

From the outside it can look as if there has been dramatic change, especially because bank leaders are taking bold stances. This week Toronto-Dominion Bank chief executive officer Ed Clark told the Economic Club of Canada that lesbian, gay, bisexual and transgender discrimination is a crucial "human rights issue" and that it won't be tolerated at his shop.

But TD and the other Canadian banks are massive organizations, and these messages only trickle down so far. The same is true for law, consulting and accounting firms. It's the subtle, day-to-day stuff that matters most, and it still isn't easy for a guy to say "I went on a road trip with my boyfriend" for the first time.

I know this from personal experience. I'm getting married this summer and my boyfriend is a research analyst at an investment bank. Save for a select – if growing – group of people, he doesn't really talk about us at work.

This struggle extends far beyond Bay Street, but the vulgar behaviour is particularly blatant in what looks, from the outside, like rather sterile office towers. It is also at odds with the perception that Bay Street is a meritocracy, because gay people often feel like they have to conform to get ahead. And it's always surprised me that such well-educated people – many top professionals have two university degrees – aren't more vocal about change.

To fully appreciate where Bay Street now stands on the acceptance spectrum, I reached out to six openly gay people – rare finds – with backgrounds in everything from private equity to asset management. In some cases their experiences were similar to mine; others weren't in such tough situations. But there was one dominant message: machismo is a lingering problem.

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The core issue, says Andrew Dale, who now works at merchant bank Acasta Capital but started out in investment banking at RBC Dominion Securities and then went into private equity at OMERS pension fund, is that so many men feel like they have to act like characters out of central casting.

The problem "is not necessarily homophobia explicitly, but it's this prototype of what a dealmaker looks like," he says. Some common traits: talk constantly about wanting to sleep with women; show no weaknesses; stick to navy and grey suits with white and blue dress shirts.

Privately, people may accept, or even support, diversity, "but there's an attitude from the top down that we should go to the rippers after [a deal's] closing dinner or that it's okay to make crude comments about women when they're within earshot," he says.

Having to conform to such a culture can be confusing for new hires.

"In some ways, you would think capital markets should be a wonderful place for equality," said Tim Thompson, the openly gay chief operating officer of TD Asset Management, because there is a belief that compensation is tied to personal performance – as long as you're making money, managers won't care how you live.

The reality isn't so clear-cut. Asset management, where profits and losses are fully disclosed, "should have been a natural place to come out, but I didn't because I didn't feel comfortable," Mr. Thompson says. Even though Ed Clark spoke forcefully about diversity in front of all of his senior managers at an internal conference in 2005, the departmental culture didn't evolve overnight. Mr. Thompson says he and so many other gay people so are prone to erring on the side of caution, raising little yellow flags in their heads if they hear someone talk about 'fags' or condone macho behaviour, that he stayed silent.

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It wasn't until 2007, when he rotated through a different group within Toronto-Dominion Bank proper, that he finally told a colleague.

Gay people are also inclined to stay quiet on Bay Street because bonus calculations are often arbitrary and subjective, says Michael Liebrock, who also works at Acasta Capital but was previously a management consultant at Boston Consulting Group. "You're not going to risk putting a big part of your compensation at risk for something that's not well accepted or understood." Bonuses are decided behind closed doors, and a single manager often calculates them, so it can feel easier to play it safe.

There are success stories. Doug Rienzo, who works at corporate law firm Osler, Hoskin & Harcourt, has been out at work since 1994 and eventually became the firm's first openly gay partner. "I never really sensed it was an issue," he says, adding that his firm is particularly progressive.

TD's Mr. Thompson is now open about his relationship and has three kids under the age of three – success on so many fronts, save for his sleep.

Yet both men acknowledge they were lucky enough to have very supportive firms. Not all organizations are as encouraging. It can be even harder for women, who face "double pressure," says Japneet Kaur, the head of support group Out on Bay Street. "One: you're a woman, and it's hard enough being a woman in the corporate world. And you also have your identity in the LGBT community on top of that."

Everyone I talked to stressed there is a continuum across sectors. Consulting firms are typically very supportive; law firms often fall somewhere in the middle; investment banking and trading are often very rigid.

Because the landscape can be so tough to navigate, one gay investment banker who spoke at Out on Bay Street's annual conference a few years back told the university students in attendance to not "act so gay" and to look "straight" if they wanted to succeed.

I know how this all sounds.

At least Bay Street's a little more civilized than the roughest parts of the mining and energy sectors. And many of the same concerns could just as easily be voiced by black people on Bay Street, or by women in capital markets, who have been fighting for promotions for two decades.

I'm not asking for special treatment. And I know there are already a slew of supportive people in capital markets. Some of them figured out my boyfriend and I were dating early in our relationship and didn't push us on it while we kept it secret for nearly two years. A good number of them are coming to our wedding next month.

It's people like them who can help change the dynamic, so long as they're a little more aware of what they condone. Gay people rarely know where their colleagues stand, so they hold back for silly reasons. It still happens to me. Even though I'm fully out at The Globe, I never bring my boyfriend up with the bank executives I interview for fear of losing access. How stupid, I know.

If you're supportive, drop little hints. Mention how happy you are that Ontarians didn't care that premier Kathleen Wynne is gay. Or tell your colleague to shut up when he's talking about yet another woman's breasts in a group setting.

To straight people, it can look like the battle is over. Gay marriage is legal here, after all. But the struggle is still very real on Bay Street, says TD's Mr. Thompson. "There is no way anybody should be saying: 'We're done, next topic.'"

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