7 Brad Pitt and Christina Applegate
Turns out Pitt’s short time with Applegate was the pits. In 1989, after the duo realized they were sweet on one another, Pitt and Applegate attended the 1989 MTV Movie Awards… where Applegate took a bite out of the young actor’s heart by ditching him for another man at the event. We’re guessing the happily married actress doesn’t regret her decision… and neither does Pitt