The Case For & Against Hooking Up With An Old Boss

Illustrated by Paola Delucca.
When you're a 20-something who hates online dating, it can feel like your only dating pool is work. After all, you spend more time at work than at home and if you work in any kind of collaborative environment, then you're likely getting to know your coworkers really well. But dating at work can be fraught, especially in the #MeToo era, and dating someone who has authority over you (like, say, a boss) is even more taboo (for obvious reasons).
So, many people choose to wait it out when they find themselves attracted to their bosses, and consider making a move once they no longer work together. I have two friends who've either dated or attempted to date an ex-boss after leaving their jobs. Kerry* had a crush on her boss for nearly two years while they worked together. When she quit her job for something new, she thought now is my chance, but the possible complications of asking out a former boss (whom she could easily work with again someday) eventually won out. She never made a move.
Then, there's Ashley*, who saw her former boss's profile while swiping on Bumble one day. She swiped right as a joke (kind of), just to see if he would match her back — and he did. They went on one terrible date. When he didn't ask her for date number two, Ashley blocked his number.
Both situations can be sticky. On the one hand, at least Ashley gave her potential romance a try, instead of being scared off because of career/dating politics. But if she'd been more reserved like Kendall, she wouldn't risk running into an awkward situation if her former boss becomes her boss again — or even an equal-footed coworker. So what do you do when you're attracted to an old boss?
I'd recommend making something like a risk-benefit analysis, which is essentially a grown up pro-con list. Think about the possible risks of making a move on your ex-boss: maybe it'll go badly and then you'll end up working together again, maybe they'll be upset that you asked and mention it to other colleagues. Then, think of the benefits: maybe you'll fall in love and end up married (hey, it happens), or maybe you don't have a happily ever after but you do have great sex for a while.
Now comes the hard part: You have to decide whether the benefits outweigh the risks. If you're seriously worried that flirting with an old boss could harm your career, then don't chance it — there are plenty of other amazing people to have amazing sex with, date, or marry. But if you don't think asking for the date will make any difference to your current or future jobs, then why not? If that's the case, asking out your ex-boss becomes just like asking out any friend or acquaintance. Sure, it's still hard, because facing rejection always is, but it's 100% doable.
If you need more courage, remember the advice relationship therapist Kate Stewart previously told Refinery29: "You regret the things that you don’t do. If you sit on your feelings and then your friend [or ex-boss] moves away or winds up in a different relationship, you'll always wonder what would have happened if you had said something."

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