Dear Career Sensei - I'm in Love with my Boss

Meetings just became more heated

Dear Career Sensei,

I'm in a fix. I think I've fallen hard for my boss!

She's hot, flirts with me, assigns the best projects to me and sings my praises to our director.
My colleagues have even noticed that she treats me differently and now refer to me as 'Teachers Pet' behind her back.

We are both single with nothing to lose should I go ahead and ask her out?

Yours Truly,

Hot and bothered


Hello Hot and Bothered,

I don't know what your company's policy is with regards to office romance but I know that office romances are largely frowned upon because they have the tendency to interfere with work and bring about conflict of interests.

Your situation is a bit dicey because of the power dynamics with her being the boss and you being her subordinate, she wields more power, at least on a professional level. Even though your colleagues are laughing about it now, they may start to resent you and feel that you went into the relationship with the intention of getting ahead (you have already admitted to enjoying some form of favoritism) .
You also have to consider what would happen in the aftermath of the relationship ending. Would you be able to continue working with her or would dive back into the job market?

While entering a relationship with your boss may be a good idea, it can be disastrous to both your professional and personal life if one or both of you are not mentally prepared for it or if either of you are not going into it for the ssame reasons.

Before you ask her about, consider these points in my earlier post on workplace romance.

All the best!

The Career Sensei

Please send your questions for publication to dearcareersensei@gmail.com