3. Christina Applegate and Brad PittPhoto: staxtopouta.gr
Long before he made friends with Jennifer Aniston or became dad to a troop of children from around the world, Brad Pitt was dumped by Christina Applegate. Acting on a mutual attraction, the duo went to the 1989 MTV Movie Awards together. Considering the fact that Christina left the event with another guy, we’re assuming the date wasn’t exactly a hit.