The 25 Worst Dates in Movies

8. Rushmore (1998)

Going out to dinner as a foursome is nothing new. But when you're the sole female (Olivia Williams) at a table with three men (Bill Murray, Jason Schwartzman, and Luke Wilson)—all of whom have romance on the brain—things are bound to get awkward. Especially when one of your suitors is an overachieving teen who professes his love right then and there, but not before offering the film's best exchange:

Max: I like your nurse's uniform,guy.

Dr. Flynn: These are O.R. scrubs.

Max: O, R they?

Dead.

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