Matthew Broderick and Jennifer Grey
It may seem a bit awkward dating someone that played your sibling in a film. The two ‘Ferris Bueller’s Day Off’ stars dated briefly in 1987 while filming the movie.
Jared Leto and Cameron Diaz
Jared Leto and Cameron Diaz started dating in 1998. Things got serious between the two because they got engaged in 2000. Unfortunately, their relationship didn’t last and ended in 2003.