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Rumored: May 2007 - July 2007Jennifer was spotted enjoying romantic meals with model Paul Sculfor and the rumor mills assumed they were dating.Photographers did allegedly spot Paul leaving Jen's home early in the morning on occasion, so assumptions were made. Dated: June 2005 - December 2006Jennifer and Vince Vaughn met during the filming of the movie The Breakup in Chicago and sparks quickly flew.

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Who has actress Jennifer Aniston dated in Hollywood?

Jennifer has a long romantic rap sheet with everyone from Adam Duritz to John Mayer.

Check out Jen's history of boyfriends and see if any of them surprise you.

Dated: April 2008 - March 2009Ever since Jen and John Mayer hooked up, they denied any reports that they were together.

Paparazzi photographed them getting cozy in Miami and the tabloids went wild.

After a series of splits, Jen and John finally made their first public outing as a couple at the 2009 Academy Awards.

Unfortunately, they split for good just weeks later. magazine claimed that Jennifer and Orlando Bloom (Brad Pitt's former Troy costar) were hooking up, but it was never confirmed.

The story seemed especially odd considering the fact that Orlando and Miranda Kerr were in a serious relationship at the time.

Dated: November 1998 - June 2000Married: July 2000 - October 2005Jennifer Aniston and Brad Pitt were set up by their agents and hit it off.

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  1. Rumored: May 2007 - July 2007Jennifer was spotted enjoying romantic meals with model Paul Sculfor and the rumor mills assumed they were dating.

  2. Photographers did allegedly spot Paul leaving Jen's home early in the morning on occasion, so assumptions were made. Dated: June 2005 - December 2006Jennifer and Vince Vaughn met during the filming of the movie The Breakup in Chicago and sparks quickly flew.

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