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Jennifer Aniston
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Jennifer Aniston Dating History

Complete list of Jennifer Aniston dates, listed in chronological order.

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On-Screen

Harry Morton

unknown date

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 ...

Charlie Schlatter

Taurus

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.

Daniel Macdonald

Taurus

1990 - 1993

Companion: Daniel MacDonald. dated in the 1990s; broke up just before Aniston was cast in Friends

Jon Stewart

Sagittarius

1994

Please add couple details

Adam Duritz

Leo

1995

Jennifer Aniston and Adam Duritz briefly dated in 1995.

Tate Donovan

Libra

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.

Brad Pitt

Sagittarius

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 ...

Vince Vaughn

Aries

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.

Matthew Perry

Leo

2006

Please add couple details

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.

John Mayer

Libra

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.

Gerard Butler

Scorpio

2009

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.

Justin Theroux

Leo

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.

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