I tended bar in a restaurant when in college, the managing partner had a daughter that was about 15-16, I was 19 at the time. She went to a parochial school nearby and used to come into the restuarant with her friends after school and grab a soda, hang out a little. Little catholic girls in little plaid skirts. Well, whenever my boss gave me a hard time, pants not ironed, hadn't shaved, I used to tease him and say "it could be worse, I could be dating your daughter", he had a sense of humor so it went over ok. Well, about 3 years later we started going out, he took it ok. I was only working part time by then. That was years ago, we're all still friends, but after that I had to tell him "it could be worse I could be dating your son" Moral of the story is, go for it.