I suspected as much, but today I confirmed that my boss is younger than me. By a lot. I am a relatively young (late 20s) male teacher. As a guy in a female-dominated field, I got used to the fact that most of my coworkers and my bosses will probably be women. MY current principal is. But the fact that she is a woman AND considerably younger than me bothers me for some reason. I can’t explain it. Fortunately she’s not too attractive. I think that would be the hardest pill to swallow – working for someone I was s******* interested in.