unknown date
Jennifer Aniston was rumored to be dating Harry Morton. According to celebrity website RadarOnline.com, the two had an intimate dinner.
Jennifer Aniston dated Charlie Schlatter. The two played brother and sister in the early '90s sit-com "Ferris Bueller," which was based on the movie "Ferris Bueller's Day Off." Despite portraying siblings on-screen, the two struck up a brief romantic affair.
1990 - 1993
Jennifer Aniston dated Daniel Mcdonald in the 1990s. The two went their separate ways just before Aniston was cast in "Friends".
Jennifer Aniston dated Jon Stewart.
Jennifer Aniston dated Adam Duritz briefly in 1995.
Jennifer Aniston dated Tate Donovan. They stayed together for three years and were engaged to be married before they went their separate ways in 1998. Aniston began dating Brad Pitt shortly after.
Jennifer Aniston dated Brad Pitt. They began dating in 1998 and were married in a private ceremony in Malibu in 2000. All seemed perfect before they suddenly split in 2005, and Aniston filed for divorce, citing irreconcilable differences.
Jennifer Aniston dated Vince Vaughn. The two 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 breaking up in December, 2006.
Jennifer Aniston dated British model Paul Sculfor. They had a brief affair in 2007 before an amicable split in late June.
Jennifer Aniston dated John Mayer. It seemed like they would have been perfect together, but they just couldn't get it to work.
Jennifer Aniston had a fling with Bradley Cooper. They went on a date at a romantic Italian restaurant called "Il Cantinori" in Manhattan. But that was apparently it. One date.
Jennifer Aniston was rumored to be dating Gerard Butler. The two 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.
Jennifer Aniston was rumored to be dating "Bounty Hunter" co-star Jason Sudeikis, but her rep denied the claims, explaining they hadn't even spoken since filming wrapped.
Jennifer Aniston is dating actor Justin Theroux. They quietly dated for a few weeks in Spring 2011 before Jennifer introduced him to close friends. In June they were seen packing on the PDA at a MTV Movie Awards after-party. They got engaged in 2012, on Theroux's 41st birthday.
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