What one movie do you never get sick of?
Some movies are just as good the 30th time as they were the first, so what flick captures your date's attention time and time again? Asking about film faves is always a great conversation starter. And even though movie choices don't tell you as much about someone's personality as their music choices, everyone loves talking about their favorite flicks. If this question sparks your date's interest, you could even take it further -- what is the scariest movie you've ever seen? What was the funniest?
And don't forget the biggest benefit of this line of questioning: It could lead to the suggestion of seeing a movie for your next date.