Should you let your son dress as a girl for Halloween again?

Answer

This is only my opinion, but I'd suggest one of his favorite characters (for instance: Spiderman) and if he doesn't like that idea, get him to go as "Cat Woman" (you could fool around with that one so there really is no gender) Two years in a row is too much and it could lead him into some bad habits.

Halloween is a safe time to experiment. Allow him to dress as he pleases, and help all you can in a supportive way. Be glad that he can tell you what he wants, and not keeping secrets. If you aren't supportive, you could create a whole dangerous world of secrets, fear and shame. Help him explore his curiousity in a safe and supportive way. Maybe it's just fun, and even if its not, its not a big deal really, as long as its not sexual or offensive to a girl in any way.