Tate Donovan, 1995-1998
Tate and Aniston met in '95 and dated for three years, with him even guest-starring as her boyfriend on Friends. The duo is said to have gotten engaged before eventually splitting, leading to her next guest-starring man.
Brad Pitt, 1998-2005
Yes, Brad did guest star on Friends (as a Rachel Green hating hottie), though not until after the couple married in a private Malibu ceremony in 2000. After seven years—and one Mr. & Mrs. Smith movie—the couple called it quits.
Vince Vaughn, 2005-2006
Another kissing costar...though this time it was work first and play later. Aniston met Vince while filming The Break-Up and the duo dated for a year (and countless engagement rumors) before eventually going their separate ways.
Paul Sculfor, 2007
Aniston took a year off from the dating scene before returning with this fine British fling. Aniston was spotted getting cozy with Sculfor, a model. Too bad he was then flung to Cameron Diaz, which, surprising, turned into a relationship.
John Mayer, 2008
Talk about an unexpected coupling. But the duo wowed the world by showing off some steamy cuddling in Miami, sparking a romance that lasted a number of months before the twosome split...for the first time, at least.
Owen Wilson, 2008
Was life imitating art? Jen and Owen starred in the feel-good flick Marley & Me together and sparked enough rumors of romance that many took it as truth. The two never confirmed and Owen went on to infamously date Kate Hudson.
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John Mayer (Again!), 2008-2009
Mayer and Aniston rekindled their romance—even attending the Oscars together!—before finally ending it again. For good. Later, Mayer would say, "I'll always be sorry that it didn't last. In some ways I wish I could be with her."
Gerard Butler, 2008
Another costar, another bout of dating rumors. Aniston played Butler's ex-wife-on-the-run in the ill-received The Bounty Hunter and, per ususal, rumors of something more quickly spread. Nothing but good chemistry was ever confirmed.
Justin Theroux, 2011-Present
The two had met in the past, but it wasn't until they reteamed on Wanderlust that romance bloomed. Jen and Justin initially denied they were dating, but eventually went public together. And now they're engaged!
Take a more in-depth look at Jennifer and Justin's Romance Rewind!