(June 30, 2007 - Source: Bauer Griffin) more pics like this »
8. Gwyneth Paltrow & Brad Pitt
Gwyneth Paltrow and Brad Pitt dated form 1994 to 1997. They got engaged when the actress was 24 and she reportedly called off the wedding because she wasn't ready for marriage.

Pitt met Jennifer Aniston just a year after their broken engagement.