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Is It OK to Date Your Boss?

Hey Thomas! Is It Ever OK to Date Your Boss?

Every month, Thomas will be answering your pressing relationship Qs. If you've got one, email and ask away!

Hey Thomas . . .

I really like this guy — he's cool, he's smart, he likes cats! The only problem is . . . he's kind of my boss. In my new job (that I really like, and would like to stay in). We've been the last two people left alone at the end of work drinks before and things got a little bit flirty. I think he likes me too. But is this a straight-up no-go zone, or can it ever work? And if it can, do we need to tell the whole office or can it be kept on the DL, at least for a little while?

Girl with a crush on her boss

Hey bo$$ lady,

Well, straight up I kind of want to date your boss. Cool? Good start. Smart? Even better! Likes cat? Purrrrfect. I'm sorry for that joke.

It's quite a pickle you've found yourself in, but it's not unusual. The reality is we spend a lot of time at work. We see our colleagues more than we see our friends and family. And I can feel it in my waters that you're an absolute winner, so it's hardly surprising that everyone in the workplace is vibing you.

I guess first things first, we need to figure out the relationship. If he's "kind of your boss" as in he's your superior but not your direct boss, then that's one thing.

When I spent a crazy Summer working at Lincraft as a stock boy, I had a wild affair with the floor manager. Until you've made love in the haberdashery aisle, you haven't lived. Anyway, I digress. She was my senior, but not technically my boss. So while it was taboo, it wasn't technically off limits.

But if this mystery man is the person you immediately report to, well then we're wading into tricky territory. It opens up a whole Pandora's box of issues. Sure it might start out well . . . side-long glances in the work kitchen, a naughty meeting request — "You, me, the conference room, no pants."

But if things do go sour, then it will not only be awkward in the workplace, but also a funny situation for him moving forward. Every decision he makes in relation to you could be viewed — by either you or your colleagues — in the frame of the relationship. If he promotes you, is it because you've got history? If he doesn't, is it because you've got history?

These are the kinds of things you need to consider. Knowing what guys are like — and I know them pretty well, I've been one for ages — it's highly likely he hasn't thought that far ahead.

Now look, I'm not saying it's a no-go zone completely, but you've got to play it carefully. You mentioned that you and your crush were the last two at work drinks. Sounds like you're both lingerers. That's totally fine, I come from a long line of lingerers and loiterers and it's something to be proud of. But if this situation is going to have legs, you need to see if it can exist in the real world. Only then will you know if it can work.

Next time the office heads out for drinks, this is what you do. While you and your pals are downing the house white and talking about how much you hate Jenny from accounts — seriously what is with Jenny, why does she only drink smoothies? — take the opportunity to slip away.

I'm calling it that your boss/future boyfriend will be a little startled and will either, a) ask you why you're leaving so early, or b) bring it up next time you speak.

It's at that point that I reckon you suggest meeting up in civilian hours. How he reacts will be your first major clue to how this is going to pan out. If it becomes a little too real in that moment and he never follows up, well you've dodged a bullet. If you do meet up and it's magic, well then perhaps it is worth exploring.

I wouldn't broadcast it to the office, but if you date for a while and people find out organically, then that's fine. But strictly no PDA and avoid being overly familiar in group emails. "Great meeting today guys, everything is on track for December. PS is pasta OK tonight babe. Or have we had too many carbs this week? I feel bloated . . . haha. Let me know. XXX."

Ultimately it pays to remember that you're taking a risk and if things don't work out down the line then you could be in for a bumpy time at work. But sometimes you also need to follow your heart and if I've learnt anything from my Lincraft experience it's that love can happen anywhere. And that calico is brutal on the body.

Best of luck,


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