Legal Question in Criminal Law in Massachusetts

Its weird, but legal to date. If you have sex then its weird and illegal (its called statutory rape or rape of a child). If the 24 year old we're coming to me for advice I would tell them that they are crazy, should up their age standards by at least two years, and are playing with fire (there's a reason they call it "jail bait"). If the 16 year old we're coming to me for advice I would tell them they are crazy, they should "date" other kids that haven't graduated college yet, and they really need to evaluate what a 24 year old is doing dating 16 year olds.

Its not a good idea. But to answer your question, there is nothing illegal about going to a movie with a 16 year old.