1. Taxi Driver (1976)
New York City cabbie Travis Bickle (Robert De Niro) has a way with women... And by that, we mean a way to ensure that a second date will never be in the cards.
After somehow cajoling Betsy (Cybill Shepherd), a beautiful young political volunteer, to go out with him, he attempts to woo her by taking her to see Language of Love, a Swedish sex film. Betsy is horrified, Travis is confused as to why. Needless to say, there's no kiss goodnight in this couple's future.
Lesson learned: Movies make for lame dates.