Is it ever worth dating the boss?

Any opinions on the topic particularly from experience would be lovely.
My boss has expressed a clear interest in me, tried to kiss me in the office, I asked him out on several occasions, he has never gotten back to me, says he would like to stay focused on his business and get it moving first. Obviously a little hurt, I have taken a big step back to lick my wounds as I put myself quite out there, to be met with frequent calling and friendly and personal chatting throughout the working day, yet he says 'go your hardest' in dating other guys, and I can't flirt with him. Don't get it, messing with me, would rather he treat me strictly like an employee. We are both extremely single, he 39 years old.


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Most Helpful Guy

  • No. A lot of the problems you are already seeing are problems that will just be magnified and far worse if you were dating. On top of that, the inherent power differential in the workplace makes it really difficult to have an equal power differential in the 'dating life'. It can become very difficult for you to make a stand if you think he could take it out on you in your career as well. And you can end up in a situation where leaving him suddenly means you can lose everything. Imagine if you moved in together after dating for a year. And he starts treating you like shit. Breaking up then means you lose your boyfriend, your place to live, and your job, all at the same time.

    Not dating co-workers is a pretty common rule, and it's a rule for a reason. It is way too easy for things to go wrong. With a boss, it's even worse. It can be terrible for you because of the power differential. But it can also open him up to potential workplace sexual harassment suits and stuff. It's a bad, bad idea.

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What Guys Said 3

  • Depends. If it can advance you to where he isn't your boss, I'd say yes. If not, then you have to question how important a job recommendation is from him in case things get ugly and you need to find a new job.

    It sounds like in your situation that he's looking for some tail if he's trying to kiss you in the workplace and has no interest in you outside of it. Could be considered workplace harassment if someone else witnesses it and would be willing to testify to it, but that would probably require that someone besides yourself has been harassed as well since people don't want to testify unless they have something to gain from it.

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  • Nope. Absolutely not.. The fallback would be really bad...

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  • Tooo risky and complicates life if others find out.

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What Girls Said 1

  • No never maybe you can get a promotion?

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