‘I had sex with my boss’ – now what?

“It was a drunken mess, and we both woke up the next morning embarrassed. I was scared I’d get fired. My boss was scared I’d tell people.”

Sex with a co-worker (let alone your boss) is awkward. But here‘s how to deal, according to sex and relationships expert Dr Gabrielle Morrissey.

It’s impossible to know how many people have dealt with this eye-wateringly awkward, heart-palpitation-inducing scenario, but fact: it does happen. Maybe you’ve hooked up with your boss at a December work do – or maybe someone who sits on your pod is (silently) trying to deal with the fallout from something that went down (ahem) under the mistletoe.

A compelling article published in Women’s Health speaks to five women who divulge what happened when they hooked up with their respective bosses.

One that was spawned by too much punch – we presume – at the work Christmas party went something like this: “[At the Christmas party] I ended up getting really, really drunk and spending the night with my boss.

“Neither of us had any chemistry or feelings for each other beforehand. It was a drunken mess, and we both woke up the next morning embarrassed. I was scared I’d get fired. My boss was scared I’d tell people. It was so awkward for the first couple of months because I directly report to him and we have meetings once a week — just us.”

But is it ever okay to hook up with your boss? Of course, we‘re talking about consensual hook-ups that occur when both parties are single. (If you’re interested in Christmas affairs, we’ve already dealt with that here) which might not be the question if the damage is already done, so to speak. But what if you’re entertaining the thought?

According to sex and relationships expert, Dr Gabrielle Morrissey, it is “never” a good idea to get busy with your manager.

“It’s a terrible idea and there will always be a power dynamic that affects your workplace and your relationships, sexual or otherwise, after a hook up or fling with your boss. Not to mention, it’s against many work policies as flirtations and sexual encounters can be misinterpreted.


“If you‘ve already handed in your resignation and have confirmed you’re leaving your job – so your boss is soon to be in no way related to you as a boss – then you could think about it, but only once you’ve left,” says Dr Morrissey.

But these things happen, right? I mean, that’s why we’re here. So if you do find yourself dealing, how can you move forward, sit in WIPS and politely ask for a rise (probably not the next day, though) if you’ve gone there?

“The most mature way of handling it – after the fact – is like any other awkward or regretful experience: talk to them about it and agree to move forward without letting it happen again.” And while the aforementioned source didn’t cite feelings for her boss (it was quite the opposite, in fact) what if you do? Or what if they caught Cupid’s arrow – and it seemed to have missed you?

Yeah … it’s messy.


“The two of you need to talk through plans and how to handle the increasing intensity of the relationship and balance it at work, without it affecting things in the office or your healthy relationship. If it‘s not mutual, end whatever is happening immediately. Otherwise, you might have to leave your job to explore other options, which might not be ideal if you like your job – or if it’s an important role for your career.”


Then, of course, there’s the office gossip. And the best way to deal, according to Dr Morrissey, is to ignore it until it goes away – which it will.

“Don’t add any more fuel to the fire. Don‘t address rumours, and let them just die away until the next scandal hits the gossip chain. Take the high road, often because rumours take on a life of their own and you’ll get caught defending against rumours that may not even be true or are greatly exaggerated. It just makes a mortifying experience more so,” says Dr Hansen.

And if you two have found love between the Xerox machine and shared kitchen?

“You need to talk openly and honestly about how to juggle the work-relationship balance and power dynamic, so that one doesn‘t absorb the other,” says Dr Morrissey.

It’s a minefield, we know.

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