Let's Talk About John Tory’s Cheating Scandal & Why Banging Your Boss Is Never A Good Idea

Is 37 years too big of an age gap?👇

Toronto Staff Writer

Political leaders sleeping with younger women is a time-honoured tradition at this point – and that's the problem.

John Tory's affair is just the latest in a long list of workplace romances gone wrong, but the stakes may not be the same for both parties involved.

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Women in the workplace have always had to be aware of sexual harassment, but what about the downfalls of consensual affairs with power imbalances and age gaps?

To bring you up to speed, Toronto's Mayor Tory, 68, admitted to having an affair with a staff member and announced that he would be officially stepping down on February 17.

The Toronto Star reported the staff member was a 31-year-old woman and that the affair lasted months.

"During the pandemic, I developed a relationship with an employee in my office in a way that did not meet the standards to which I hold myself as Mayor and as a family man," said Tory.

"The relationship ended by mutual consent earlier this year. During the course of our relationship sometime ago, the employee decided to pursue employment outside City Hall and secured a job elsewhere."

Tory claims that the relationship was consensual, but as we work through what this means for women in the workplace, it is important to note that so far, we've only heard one side of the story.

Sex, relationship and family therapist Jenifer Smith questioned when these cliche relationships will stop and when a no-tolerance rule will be set in place for workplace romances.

Power dynamics

Infidelity and the effect that has on Tory's wife and family aside, the power dynamic of his public position and being someone's boss is pretty skewed.

Smith said women are often attracted to men in power due to their "grandiose" appearances, but at the end of the day, that person is still your boss.

"If things are going great, then they can treat you great. They could even give you a promotion, increase your pay, or you just get extra perks like extra events or taking private planes," she explained. "But when things are not so good, that's when it becomes a scandal. Now you make you're losing your job, it's gonna be much harder for you to get hired somewhere else."

Smith noted that public affairs tend to follow you around, and if we look at history, the mistress often gets the short end of the stick with an added layer of misogynistic scrutiny and slut shaming.

Dating your employee may not always be an abuse of power, according to Smith, but it does come with some caveats.

"I don't think it's always the abuse of power, sometimes two people really have a connection. But early on in the relationship, you have to have that conversation of, okay, if we really want to pursue this, then somebody else is probably gonna have to go work somewhere else," she said.

Although I'll leave it up to you to guess which party is most likely to leave their position, someone in a management role with more power or an employee.

Age gaps

A 37-year age difference is a taboo, but according to Smith, an age gap may be the least concerning part of this "messy" situation.

"From the sex therapist's perspective, it is sometimes just about libido, it is about finding somebody who matches your sex drive or someone that kind of matches your energy. You know, even though he's older, he may have like a young spirit or, you know, have a strong libido," Smith said.

"I feel like in any of these storylines, there are big age gaps, but a lot of it is to do with just matching each other's energy."

December-May relationships between men and women are actually more normalized than you might think.

Smith said men are often praised for dating younger women, while women are still criticized and labelled as cougars when it comes to dating younger men.

"You realize with men, older men and younger women. There's not really a name for it."

What does this mean for women in the workplace?

Women have their own agency and the power of choice.

You can choose to enter a consensual workplace romance, but you need to be aware that a bad outcome may not play out in your favour.

Smith brought up Monica Lewinsky, a writer and anti-bully activist who had an encounter with former U.S. President Bill Clinton while she was a 22-year-old intern.

Despite the massive power imbalance in that relationship Lewinsky became a household name and was widely shamed for years.

"Look at Monica Lewinsky and how long now we've been talking about her. That was a consensual encounter, but it's still something that people talk about, and she's really been ridiculed for like 20 years," Smith said.

While Clinton faced his fair share of jokes, the narrative between these two is still widely different.

Clinton is still remembered for his accolades, and his extra material affair is a smudge on his legacy, but for Lewinksy, that was her whole story for years.

"Sure, my boss took advantage of me, but I will always remain firm on this point: it was a consensual relationship. Any 'abuse' came in the aftermath, when I was made a scapegoat in order to protect his powerful position," wrote Lewinsky in her 2014 Vanity Fair feature.

Smith said the continuation of these stories may mean there's a need for a zero-tolerance policy.

"I feel like there needs to be some type of policy, right, a zero-tolerance policy of if we find out any fraternization, you're terminated, and it's both people, not just one," she said. "If you consent to this, you know, what you're putting on the line, and you have to really be taking into consideration of, 'Am I willing to risk all I've worked for, for this person?'"

Cheap advice: Should you date your boss?

You can't help who you are attracted to, but you can decide whether or not to act on it.

Smith's stance is a strong no, and I have to agree.

Regardless of your gender, dating your boss is a recipe for disaster, and the slim chance that it could be true love is greatly outweighed by the cons.

First off, to have a successful relationship, one of you is most likely going to have to leave your job after notifying HR, and that isn't a small sacrifice.

At the time, you may be willing to compromise your job for your honey, but who knows what career angst and resentment could be waiting to pop up down the road if things don't go as planned.

If you both decide to stay at the workplace, this can make things awkward for your coworkers, too, according to Smith.

"I've worked in multiple places where people were spouses, and it made for a very tense environment at times. When someone was being ridiculed for their work performance, and then their spouse is trying to take up for them. And it's like, oh, gosh, like, you guys gotta leave the marriage part out of this," she said.

If your boss is coming onto you and you're feeling pressured, Smith added it's important to remember that you do have a choice and options to help you.

"People have to be in the mindset of, 'I don't have to do this, if I don't want to,' of being able to go to HR, you know, and take it up the chain."

Smith encouraged people to keep a track record of any type of unwanted courting, from someone asking you out, calling you at home or making sexual comments.

"You want to document all of that, put it in a journal, keep it in a Word document or something where you're just tracking it, and then take it to HR and let them know."

If a relationship is consensual in the workplace, I'm not here to judge anyone, but it is important to know that in the world we live in, the fallout isn't always fair.

This Opinion article is part of a Narcity Media series. The views expressed are the author's own and do not necessarily reflect the views of Narcity Media.

This interview has been condensed and edited for clarity.

Cheaper Than Therapy is a spicy new column and video series hosted by Brooke Houghton where readers can share their own anonymous questions and get expert advice for free. Brooke speaks from her own experiences as a single 20-something woman in Toronto and brings on expert guests from therapists to celebrities to help solve your relationship, sex and love issues. So if you can’t afford therapy from an actual professional, ask her a question here and tune in next month for another episode of Cheaper Than Therapy.

Brooke Houghton
Toronto Staff Writer
Brooke Houghton is a Staff Writer for Narcity Canada's Ontario Desk focused on celebrity news and is based in Toronto, Ontario.