Lennie - I have a huge crush on my boss! He's never made any advances towards me, and he never talks about his private life, so I don't know what his relationship status is (where's Facebook when you need it?) How do I tell him how I feel without....making it weird at work?
Dear Work Weirdo,
No matter what you risk making it weird at work by expressing interest in your boss. It's never a good idea to mix work and play, but it happens all to often in the work environment. The average relationship lasts 5-7 months, so the odds are you're going to wind up working for your ex-boyfriend. So think of that first and foremost. If you still cannot help yourself, I would find out the company policy on dating co-workers, then I would try to find out his relationship status as discreetly as possible. Maybe you can find out what he does in his non-work hours and arrange a meet-cute. You know in the romantic comedy movies where the leading couple first meet in some cute way. Do you know where he works out? Where he has coffee? Coincidentally, just bump into him there while looking your absolute best and strike up a casual conversation. If he's interested, he might just give you an indication outside of the work environment. But, whatever you do don't become a stalker!