So this advice isn't for me, but a friend. He's a senior, taking a sophomore to prom this year. She's very attractive, could pass for older, and he is smitten. Has already told her he's nervous because she's so pretty. She has a boyfriend, but really wants to go to prom, she even asked one of his friends earlier this year to take her(which he doesn't know about.) He didn't even ask her himself, it happened through a friend... long story short they are going on a trip to the city (NY) alone, to go see the museum of modern art, so as to acquaint themselves before going to prom together. He wants it to be a date and knows she actually likes her bf, and was asking me for advice. Things like should he pay for her, etc. I've been checking this subreddit out for a while and was giving him basic principles and he said what I was saying made alot of sense and he wanted to be able to act more alpha (he's a shy kid). So I turn to you TRP, what should he do?