Jennifer Aniston » Dating History

Historical look at Jennifer Aniston relationships, listed in date order.

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Harry Morton
Jennifer Aniston and Harry Morton unknown date RUMOR
Forget speculation she is back with on-again, off-again flame John Mayer because Jennifer Aniston has a new `friend` in her life, RadarOnline.com can exclusively reveal. The actress is set to ignite rumors that she has a new boyfriend after she had an intimate dinner on Wednesday night with a handsome ... [more]
Adonis Tsilimparis
Adonis Tsilimparis and Jennifer Aniston unknown date RUMOR
Dated when they were in seventh grade. [more]
Charlie Schlatter
Jennifer Aniston and Charlie Schlatter 1990
Jennifer Aniston and Charlie Schlatter played brother and sister in the early `90s sit-com `Ferris Bueller,` which was based on the movie `Ferris Bueller`s Day Off.` Despite playing siblings on-screen, the two struck up a brief romantic affair. [more]
Jon Stewart
Jennifer Aniston and Jon Stewart 1994 RUMOR
Adam Duritz
Adam Duritz and Jennifer Aniston 1995 RUMOR
Jennifer Aniston and Adam Duritz briefly dated in 1995. [more]
Tate Donovan
Jennifer Aniston and Tate Donovan November 1995 - August 1998
Jennifer Aniston and Tate Donovan stayed together for three years and were engaged to be married before they split in 1998. Aniston began seeing Brad Pitt shortly after. [more]
Brad Pitt
Brad Pitt and Jennifer Aniston March 1998 - January 2005
The Brad Pitt and Jennifer Aniston marriage was considered one of the rare Hollywood success stories. They began dating in 1998 and were married in a private ceremony in Malibu in 2000. All seemed perfect before they suddenly separated in 2005, because Brad Pitt cheated on Jennifer Aniston with Angelina ... [more]
Vince Vaughn
Jennifer Aniston and Vince Vaughn June 2005 - December 2006
Jennifer Aniston and Vince Vaughn were first rumored to be dating while filming `The Break Up` in 2005 before going public later that year. The lasted for more than a year before officially splitting in December, 2006. [more]
Matthew Perry
Jennifer Aniston and Matthew Perry 2006 RUMOR
Paul Sculfor
Jennifer Aniston and Paul Sculfor April 2007
Jennifer Aniston and British model Paul Sculfor carried on a brief affair in 2007 before an amicable split in late June. [more]
John Mayer
Jennifer Aniston and John Mayer April 2008 - March 2009
John and Jennifer both have a history of dating other high-profile celebrities. It seemed like they would have been perfect together, but they just couldn’t get it to work. [more]
Gerard Butler
Jennifer Aniston and Gerard Butler June 2009 RUMOR
Jennifer Aniston and Gerard Butler were almost as secretive as they were close following the filming of `The Bounty Hunter.` While neither have ever confirmed that they so much as went on a date, they were spotted several times in some very close situations. [more]
Justin Theroux
Jennifer Aniston and Justin Theroux May 2011
Since May 2011, Theroux has been in a relationship with his Wanderlust co-star, Jennifer Aniston. Theroux proposed to Aniston on his 41st birthday and they publicly announced their engagement on August 12, 2012. [more]

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