We all love our celebrities, especially when they pair up. But sometimes their tastes when it comes to matters of the heart can leave us scratching our heads.
12 / 38
Rose Prouser/Reuters
Adam Duritz and Courteney Cox But when Duritz and Aniston broke up, he wasn't yet done with the stars of "Friends." Duritz went on to date Aniston's co-star Courteney Cox in 1997, leaving him short a date with Lisa Kudrow from dating all three lead actresses on the sitcom.