Celebrity News
Tate Donovan, John Mayer and More of the Men Jennifer Aniston Dated Before Finding Love With Jim Curtis
Adam Duritz
In 1995, Jen briefly dated the Counting Crows frontman, 61, who years later fondly recalled to Entertainment Tonight how “nice, really funny [and] really pretty” she was. Bestie Courteney Cox dated him in 1997.
Tate Donovan
The O.C. star, 62, who Jen’s praised as a “good guy,” fell for her in 1995 after splitting from Sandra Bullock, 61. Tate played her love interest on Friends in 1998 — just as they were breaking up in real life.
Brad Pitt
To Jen, Brad was “just this sweet guy from Missouri” when they got together in 1998, she told Rolling Stone in 2001. They divorced in 2005, nearly five years after their Malibu wedding, amid his emotional affair with Angelina Jolie.
Vince Vaughn
Jen’s The Break-Up costar, 55, was her first boyfriend after Brad. “I call Vince my defibrillator. He literally brought me back to life,” she told Vogue of their year-long romance that cooled in 2006.
Paul Sculfor
In the summer of 2007, Jen spent time with the British model, 54, a former boxer and construction worker. Post-breakup, he dated Cameron Diaz, 53. “We still message now and then,” he revealed to Hello! magazine in April.
John Mayer
After their on-off two-year romance ended in 2009, the singer, 48, criticized Jen’s aversion to social media, telling Playboy “she’s still hoping it goes back to 1998.”
Justin Theroux
In 2011, Jen and her Wanderlust co-star went public. He proposed a year later on his 41st birthday and pal Jimmy Kimmel officiated their backyard wedding in 2015. Two years later, it was over.
