10 celebrity serial daters you didn’t know (With Pictures)

9. Jennifer Aniston

At some time or another we have all felt for Jen Aniston. Back in 1998 when she married Brad Pitt the two seemed perfect together. However, in 2005 the marriage came to an end when Brad had an affair withAngelina Jolie. This heartbreak sent Jen on a serial dating spree.

The spree began when Jen dated her The Break Up co-star, Vince Vaughn. When that ended after a year, she went the bad boy route and started dating John Mayer (who obviously made our list too). That came to an end and Jen had a brief secretive hookup with Gerard Butler. A few flings later she finally found true love in 2011 with her now husband Justin Theroux. Like Mom always said, “Sometimes you have to kiss a few frogs to find a prince.”