Allison Bradbury in The Sure Thing (Played by Daphne Zuniga)

Walter (John Cusack) and Allison (Daphne Zuniga) are obviously perfect for each other, but he of course pines for the blonde, mysterious “Sure Thing” of the title (Nicolette Sheridan).

Through a long series of road-trip misadventures, Walter and Allison develop a close affection for each other that finally turns into something more when Walter realizes that he doesn’t feel true love for The Sure Thing.

It was released in 1985, the same year as the next film on our list.