Jennifer Aniston Engaged: A Look Back at Her Former Flames

Tate played Jen's love interest on several episodes of "Friends." Their off-screen relationship lasted from 1995 to 1998.

Following her shocking divorce, Jen dates Vince Vaughn, her co-star from "The Break-Up." Engagement rumors start to swirl until they really do break up in 2006.

In 2008, musician John Mayer was the next beau to win Jen's heart. The two dated on and off, but finally called it quits weeks after the 2009 Academy Awards.