What pogre said--don't assume that because you heard somewhere that some state has a "Romeo and Juliet" law, that you're OK, or that 16 is probably old enough. Every state varies. And if you're a heterosexual couple, there's that little "contraceptive failure" issue to worry about, y'know?
I have generally dated older guys and only once dated somebody significantly younger (never. again. NEVER!). My husband is 12 years older. My observations--
--The age gap looks very, very different from the older side. When I was a teenager, the idea of dating a college-age guy seemed perfectly normal. When I was college-age, I could see that the guys my age who dated high-schoolers did so because they saw those girls as cute, easily manipulated and disposable. I myself dated somebody "just legal" when I was a law student. He got very badly hurt, because I mostly saw him as somebody cute and fun to hang around, while he, being inexperienced in relationships, really had no frame of reference for dealing with his emotions about the whole thing.
--The age gap matters more when you're younger. 14 and 20 is a much bigger gap than 40 and 50.
--LIfe experience matters more than numbers. When I met my spouse, I'd already been living on my own, had been married and divorced, and gone to law school. If I'd been typical for my age at the time and had just gotten out of college, we would have had a lot less to talk about.
and here I am having waded through Undergrad and some Graduate courses and now Law school; I've little to say that they can relate to
Try the misogyny jokes! Older chicks think they're adorable.