Jennifer Aniston

This list would not have justification if we didn’t mention one of the most high-profile breakups in Hollywood history.

Jennifer Aniston and Brad Pitt’s relationship was one of the most picture-perfect unions in the early 2000s. Dubbed as a power couple, Jen and Brad dominated Hollywood’s dating scene seven years before ending their marriage in 2005. The former couple then moved on to different people, with both actors re-marrying and expanding their individual investments. Jen, in particular, dated musician John Mayer after her breakup with Brad. Later on, she met and married Justin Theroux but eventually broke up with him. So who is the actress dating now? Well, rumor has it that the actress is now in love with a dashing new beau that has never seen her hit sitcom FRIENDS. Whoever that lucky man may be, we just hope that he takes care of America’s darling.