Best Answer - Chosen by Voters Unless the two of you had a friendship prior to your going to work there, or unless you are good friends (as in, you go out for beers and he helps you fix up your old car "good friends") now, yes, it's quite odd. I really have no reason to talk to my boss about my sex life and he has no reason to ask. Work is work and home is home. Occasionally he will ask how my girlfriend's doing, whether we had a good time on vacation, how my parents are... but that's cordial office small talk. If he were to ask, "Hey, how many times has your girlfriend had an orgasm during sex?" I'd tell him that's between me and my girlfriend.