22. The Sure Thing (1985)
Walter "Gib" Gibson (played by a teenage John Cusack) has a hard time getting girls while going to school in New England. Enter Allison Bradbury (Daphne Zuniga), a beautiful girl in his English class. Gibson tries to holler at homegirl, only to get shut down, so his buddy tells him about a girl in California (played by a 22-year-old Nicollette Sheridan) who he can definitely hook up with.
Gibson hitches a ride to California for this "sure thing," but so does Allison, and they end up having to ride the entire way together. Since this is John Cusack we're talking about, you can guess how things turn out.