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Dating Your Boss? 6 Reasons Not to Date your Boss


Forced to spend time together every day, it’s not unusual for two people in a boss-subordinate relationship to develop romantic feelings for each other.

Usually dating works best when you act naturally and follow your instincts, but not in this case. Ultimately you could be choosing between love and your career, so before you make the first move, or reciprocate your superior’s advances, heed these reasons not to date your boss.

1. Colleague Out-Cast

Nothing will alienate you faster from your co-workers than going to bed with the boss. Either you have to keep it a secret, tainting your work-based friendships with deceit, or you tell all and suffer their disapproval.

Colleagues will disagree with your choice of mate for a number of reasons. Some will be vexed that you’ve beaten them to it, others will be concerned you will benefit from preferential treatment. Many will also alter their opinion about the boss, so it’s not just your career that suffers but their’s too.

2. No Safe Sounding Board

After a tough day at work, many people like to come home, pour a glass of wine and spend ten minutes venting about their idiot boss to their loved one. But wait. What happens if the dearly beloved you come home to is your idiot boss? Now who are you supposed to off-load on? Calling your mother or friends won’t work either, because they will not want to get caught in the middle of this muddled mess you have made for yourself.

3. Merit vs Favouritism
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You will never be sure whether praise, promotion or pay rises have been earned on merit or awarded in favouritism. Worse still, even if you are convinced you are worthy of recognition, many of your colleagues will be adamant your perks are a result of being the boss’ bit on the side.

It’s the same deal with criticism. If an idea gets canned, or you get a ticking off, will you believe it’s fair, or will you be blaming last night’s argument over what to watch on TV?

4. Salary Negotiations

Salary negotiations between manager and subordinate usually follow a set script:
Boss: You have worked really hard this year, and we want to recognise your contribution, but please remember we are restricted to tight budgets yadda, yadda, yadda, some words that basically mean your pay rise will be small.
Subordinate: I appreciate that, but I think I’m worth more, and I have financial commitments…yadda, yadda, yadda, some words that mean you are a responsible adult worthy of a grown-up pay packet.
And this goes back and forth a few times until a reasonable increase is decided.

Now imagine that your boss knows that instead of investing money in something sensible, you are actually blowing it every weekend on alcohol and clothes. How awkward will those negotiations be now?

5. Break Up Fall Out

If dating your boss is bad, breaking up with your boss is worse. You may find some emotional release by spitting in his coffee every morning, but otherwise pretty much every day will be filled with heartache and pain.

6. Against Company Policy
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This is the most important reason to consider. In a lot of companies it is against company policy for co-workers, especially of different seniority levels to date. If you think your love is the real deal, one of you will need to change jobs, which puts a lot of pressure on the relationship.

Online Alternative

When people spend a lot of time at work the pool of singles in the office may be the only potential dates they meet. Joining a free online dating site can open up a whole world of eligible people, who you don’t have to face over the water cooler every day.