When Career Advice = Dating Advice

I was aware that he had a contentious reputation. Male coworkers called him “a joke” and described his primary job responsibility as making the rounds on the floor and flirting with women. Female coworkers told me that he gives them “weird and disingenuous vibes.” A director in my group called him “a political animal” and advised that I keep my head down and stay out of his way.

We met in my early days at the company. Three years later, he became my manager’s manager, unseating the previous manager in a well-orchestrated office coup. For me, and for the majority of my teammates, the change in leadership took us by surprise. No one saw it coming. But I guess that’s how coups usually go.

Our working relationship had always been tenuous in my mind. He was older, he had a family, and he was my superior — and yet, every interaction centered around his teasing me. It made me nervous. At first, I was perpetually caught off guard, stunned and blushing. Later on, I was told by another coworker that, “if he makes fun of you, it means he likes you.” So, with time, I learned to adapt, to go along with his humor, and, on the rare occasion that I recovered my balance before he walked away, answer with my own witticisms.

One day, he stopped me at a crosswalk as I was leaving work. He told me that he had been “hearing good things” about me and the work that I’d been doing. I was flattered, proud.

In turn, I happily asked him, “do you have any advice for me?”

He smiled mischievously and said, “Advice? Sure. I think…you should date Leon.”

Wait, what? I was asking him for career advice, not dating advice. Did he really tell me to date a mutual coworker (and friend)? How was I supposed to respond to that? What was the appropriate, expected response to this? Was there one? I couldn’t decipher how serious he was, or decide whether it mattered. In the moment, all I could do was laugh nervously and shrug it off.

I’m not sure that that was the best response. In hindsight though, I don’t believe that there was much of an alternative.

This became a recurring and favorite inside joke of his throughout the next months. I’m an instinctively private person — perhaps to a fault — but I informed him that I wasn’t available, that I had a boyfriend. That didn’t seem to matter to him. During one out of every three of our conversations, he would suggest — with raised eyebrows, a gleeful look in the back of his eyes, a fleeting smirk — that I give Leon a chance.


In the inaugural article of this publication, I stated that it too often falls on women to prove their ‘seriousness’ when networking with men. The same seems to be true when women are working to advance their careers by hustling in their day jobs.

The following three months were tumultuous. The company was restructured and personnel moved around. Leon’s workplace wingman showed himself out for another opportunity.

On his last day, he gave me a big bear hug goodbye, telling me that he had always been an advocate of mine. In what sense?, I wondered, and to whom? What about me were you advocating for?

Weeks after his departure, I found myself at a coworker’s get-together, exchanging anecdotes about him with another teammate. She mentioned that, in addition to the flirtatious teasing, he had a habit of gossiping about and disparaging his reports to one another. It was scandalizing, inappropriate — and yet, for him, it was completely unsurprising.

What is surprising though, is that we, as a company, allowed this behavior to continue, that we remained silent and consequently, complicit. We heard the stories whispered through the grapevine and we warned each other against working on his teams. But that was all. And that wasn’t enough.

I remained silent because I was well aware that it was his territory more than mine. He determined the rules more than I did. It was his game and, even though I didn’t know all of the rules or understand the objective, I knew that only I could lose.

So, how can we change the game so that it’s not up to us to prove that we belong here too? So that we can play on our own terms, not by someone else’s rules? How can we change the game so that it’s not ours to lose?


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