JK,

This is one of those times that a crystal ball would really come in handy. You haven’t really told me much about your predicament… My gut says: don’t do anything.

I will more or less stick with that answer, depending on a few factors. Like: are either you or your boss married to other people, dating someone or completely free and easy? Are you both heterosexual (and of opposite genders) or vice versa? What kind of career do you have? How important is that career to you? How big is your industry? Do you have a history of dating co-workers or bosses? Are there rules and regs at your Company about dating co-workers?

Since you’ve kept your question short and sweet I’ll let you figure out which side of those questions you’re on. The most important thing you can do in your predicament is consider the consequences. Firstly to your job or career, also to whatever responsibilities you have (e.g. mortgage, family to provide for etc.) then to any relationships that may already exist.

The other thing I’d think about is this: how long is this person going to be your boss? If  you work at the kind of place that people move around quickly, you may not have to explode your brain worrying about this. You could be free to hit on this person in a few months!

I don’t mean to sound like a downer when it comes to love. Reading my answer I’ve almost surprised myself – so pragmatic!! But the reality is; you probably don’t know how this person feels about you and taking a chance could hurt your career, his / her career or both. Of course it’d be worth it if your boss happens to be madly in love with you too, but what if they aren’t?

Your best bet is to be safe and  just play the waiting game. If it’s meant to be, fate will find a way of putting you together.

Good Luck!

AB

Alexis Brown