I can understand not letting your high school daughter DATE a 23 year old, but a special prom thing like this? I don't see any downside. Its not like Hill is cruising for easy high school girls, lord knows NBA players, even semi-obscure rookies like Hill, can have all the easy groupie tail they want. He's just doing a nice favor for a girl. Plus, his assistant is going as a pseudo-chaperone. I don't see anything wrong with it.
I think its sweet and classy. It would be like Ashton Kutcher or Shia LeBoeuf taking a fan to her prom. Not a big deal at all.