Sleeping With Your Boss

Emma Tonny continues her column with sage advise on sleeping with colleagues; specifically - your boss. Drawing on her own experience she reveals all about how things inevitably play out…


Don’t fuck your boss. I know that now I’ve said it you want to; but seriously just don’t get there. Stop thinking about them right now. No, I mean it: stop!

As we’ve already established in past articles you end up quid’s out because you have to buy the most expensive wines and it’s just not worth it. Obviously, it seems like an enticing option at the time or no one would do it, but you gotta think bigger picture. I mean I didn’t… but I was advised to and I always pass on good advice rather than taking it myself.

My boss was older, wiser (probably not true, but it flows well) and was in charge- ultimate sex appeal, am I right? Training someone and the infamous work place ‘role play’ lends itself to endless eye rolling and cheeky suggestiveness. You’re locked into a close-knit encounter where someone’s sole purpose is to ensure that you’re good at your job. The intensity can be seductive in itself, but just try to keep some sense of perspective about the longevity of your role with this company. Or, do what I did and think FUCK IT! You don’t want to work their long term anyway and he’s gorgeous so why not go for it?

You’ve heard of love at first sight, but have you heard of lust at first hearing? I absolutely guarantee you it’s a thing. The first guy to train me at my remarkably brief time temping at a call centre was absolutely not the guy I went on to sleep with. I’m sure he’s lovely but it took him half an hour to get to the point and even after he did, I wasn’t entirely sure what the point was. I almost didn’t go back, but what I found on my second encounter, at the surprisingly beautiful building this call centre had been abandoned in, kept me going back for more.

Tall, dark and handsome, he had a voice that would send tingles up the most resilient of spines. As someone with almost no backbone whatsoever when it comes to darkly attractive people, I had little intention at all of holding out. Swivelling aimlessly on a chair that had stuffing starting to sag out the sides, I heard his voice on the stairs and new instantaneously that this was a problem.

Fast forward through our flirting and my hopeless, tragically anti- feminist pretence that I didn’t understand anything to ensure more ‘training time’ and you find him at my house party a few months later. I’ve obviously quit the job for something far better and, equally obviously, we’ve agreed that nothing is going to happen. Absolutely nothing. He was my boss. He’s much older. We have colleagues in common. It would be weird and is totally, definitely, definitively NOT gonna happen.

So, I mean, obviously it happens.

Don’t: risk a career you care about to sleep with someone at work.

Do: sleep with your boss if you don’t really care about the job. It’s fun.

What I learnt: decisions are often only good or bad as the outcome determines, so you may as well roll with the punches.