Originally posted by: ricarleite
If she's more of an intelectual, I'd recommend the Kubrick classics, Dr Strangelove, 2001 A Space Odissey, Eyes Wide Shut. In that order.
If you feel she won't dig these kinds of films and is more of a crime or action flick fan, I'd go for Pulp Fiction, Memento and Ran (or any Kurosawa film prior to 1985).
Or go for three movies that wont fail: Sleepless in Seattle, Casablanca, As Good as it Gets.
Yeah, Pulp Fiction rocks, also Reservoir Dogs.