Who: Paul Sculfor
When: May 2007 – July 2007
What: The pair were found enjoying romantic dates together on numerous occasions which of course gave rise to the rumour that the two were romantically connected. Photographers also apparently spotted Paul leaving Jen’s home early in the morning several times, which added to the speculation.
Who: Orlando Bloom
When: April 2008
What: It was OK! magazine who claimed that Jen and Orlando Bloom (who costarred along with Brad Pitt in Troy) had a bit of a fling. Even so, this was never verified and seemed particularly unlikely as Orlando and Miranda Kerr were in a serious relationship back then.
Who: Adam Duritz
What: This was a short affair with the Counting Crows singer who actually continued to date Courteney Cox (Jen’s buddy and costar in Friends) immediately after they split up.
Who: Tate Donovan
When: Dated: 1995 – 1998
What: Jen and Tate were engaged for some time but ended their relationship shortly after. Tate guest-starred in Friends in early 1998 as Jen’s love interest for 8 episodes.
Who: Paul Rudd
What: Jen met Paul Rudd during the filming of The Object Of My Affection in 1998. They dated for about one year.
Who: Brad Pitt
When: November 1998 – October 2005
What: Maybe the most well-known Jen liaison, Jen and Brad were married in July 2000. They met when they were set up by their agents, and hit it off immediately. In fact they openly admit that they practically moved in together after their first date. They had a million dollar wedding inviting 200 guests, with 50,000 flowers, a gospel choir, and fireworks at the wedding reception. The couple separated in January 2005 amid rumors that Brad and Angelina Jolie (his costar during the time) were having an affair. Two months later divorce proceedings had begun and in October the marriage ended permanently.
Who: Vince Vaughn
When: June 2005 – December 2006
What: Jen met Vince Vaughn in the filming of the movie The Breakup. They immediately hit it off and became a couple. It became hard to separate between romantic stills from the film and actual photos of the two off set. About a year into their relationship there were rumours that the couple were engaged. On the other hand, within another six months the couple had formally split up.
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