Oooh, Melting Pot, definitely!  Which also solves the reservation problem, since you have to have them there.  Just don't forget to bring a Tide stick... We went for my 24th birthday and I spilled chocolate fondue on myself, but the waitress had one of those and it fixed it )
Order a bottle of wine with dinner, then he can help you pick )
Yes on underwear.
Movie tomorrow )

If you live somewhere in the southern part of the state, I suggest French Lick wine or Huber wine.  Great local wineries that sell in liquor stores and grocery stores.