Pretty In Pink — 10 Films With Lousy First Dates

Participants: Andie (Molly Ringwald), a poor-but-resourceful teen girl; and Blaine (Andrew McCarthy), a rich and snooty blue blood.

Circumstances: In this tremendous clash of cultures and financial ideology, neither participant finds it terribly comfortable going in each other's circles. Blaine asks Andie out, which leaves her thrilled, but it's slow going at first.

What Makes It Awful? First, Andie is really turned off by the rich-boy house party (held by the incomparable James Spader as 'Steff') Blaine takes her to, so they leave to crash her local hang-out, an altsy music club, but once there, her best friend Duckie Dale (Jon Cryer), who's forever had an enduring crush on Andie, calls Blaine a "buttwad" and things descend from there.

Outcome: Once alone, away from the prying eyes of others, they seem to really hit it off, but Blaine ends up listening to Steff and dumps her before the prom, a move he quickly regrets. They end up happily in each other's arms in front of Blaine's BMW convertible with O.M.D.'s "If You Leave" playing on the soundtrack.