8 Dos And Donts For Dating Your Boss

Women's Dating

8 Do’s and Don’ts for Dating Your Boss


Written by: Lovestruck.com


Lovestruck.com is a multiple award-winning online dating site that lets you date other singles who live, work or simply are nearby. Lovestruck users are predominantly quality, busy city-based people who are looking for amazing dates with like-minded people. Simply meet them over a coffee or something stronger to see if there's any chemistry. We believe online dating is an amazing way to broaden your opportunities to meet new people, but we want to get you offline and dating as soon as possible. There's nothing like falling in love, and there's no one like Lovestruck for making it happen.

Edited by: Lillian Castro

Lillian Castro

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Lots of people like to flirt at work (let’s face it, it’s fun), but what if an office relationship turns into something more? And more to the point, what should you think about when it comes to dating your boss?

Here at Lovestruck.com, we know most people would shout “BAD IDEA” very loudly at you if you even mentioned the possibility of taking your boss to bed. However, we know love strikes in the most unexpected of places, like in the boardroom, by the photocopier and on those all-important team-bonding away days.

Avoid office gossip, awkward meetings and desk-based dramas with Lovestruck’s foolproof guide to dating your boss.

1. Do be professional.

Don’t mix your personal and professional lives. Between 9 a.m. and 5 p.m., keep the relationship on a work-only basis.

Avoid PDAs like lingering looks, long lunches together or a quick trip to the stationary cupboard when the moment takes you. You can’t be seen to let the romance affect your productivity in any way. Remember you are being paid to work.

If you want to see each other after work, arrange to meet outside or even at a bar or coffee shop nearby at a pre-agreed time. Make sure the coast is clear before you revert into couples mode.

2. Don’t email each other.

While it is so tempting to send emails at work and start the flirty chat during the day, this is just a terrible idea.

Aside from the fact that most IT departments can access your inbox remotely, one slip of a finger on “reply all” and your whole team will not only know you are dating the boss, but they’ll know exactly what you plan to do to each other later.

3. Do be discreet.

When you fall for someone, it’s pretty hard to not shout it from the rooftops, but tell your workmates carefully or not at all.

If you do tell them, it might make them more wary of your motivation – or they could be jealous if you get promoted or land a good gig. There is no right or wrong here, but approach the water cooler chatter with caution.

4. Don’t go too fast.

Just because you see each other at work, that doesn’t mean the relationship has to go at breakneck speed. Take it slowly and it’ll have more chance of working out in the long term.

“If you’re seriously into your boss,

it might be worth moving teams.”

5. Do remember you’re equal.

It can sometimes be hard to separate your work and personal relationships. Yes, at work you are your partner’s subordinate, but outside of work you are their equal. Make sure they treat you that way. If you ever feel disrespected, talk about it.

6. Don’t bring it home.

So he didn’t like your idea in that meeting? Or he spent a long time with your colleague discussing something? Don’t let this affect your romance.

This is a toughie but if you’re dating the boss, then you’ll need to learn to handle it.

7. Do have a plan B.

If you are seriously into your boss and think the romance could last the distance, it might be worth asking to move teams or looking for another role elsewhere.

This is also worth thinking about in case it all goes wrong and you split up, as this opens a whole new can of worms. If you’re determined not to move, consider having a breakup contingency plan.

The Brits would say, “Yikes! Young lady, make sure you approach dating your boss with caution.”

8. Finally…

Never try to photocopy your backsides. Obviously. You could both end up in ER…

The Brits would say, “Crikey! Now look here, young whipper-snapper. Make sure you approach this whole dating your boss business with extreme caution.”

Americans would say, “If you’re gonna do it, you need do it right.”

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