Classic Italian? Oh boy. I know some good pizza places, but I haven't hit an Italian place unless it's actually in Italy. You want to take your dates to Italy? Go here: [address] That place is fantastic.
I know it's not like classic French stuff, but Le Bernardin is good. Chef's a nice guy. Per Se is pretty good too, but the menu is one of those daily tasting things, so it changes a lot.
It'd be easy to bump you up with a reservation too. Just have to let us know when...you're really gonna dive into the dating pool, huh?