| Jennifer Aniston Dated Aug 27th 2011, 10:04 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. John Mayer 
Photo: Stephen Shugerman/Getty Images Dated: April 2008 - March 2009 Ever 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. Orlando Bloom 
Photo: Chris Jackson/Getty Images Rumored: April 2008 OK! 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. Paul Sculfor 
Photo: Dan Kitwood/Getty Images Rumored: May 2007 - July 2007 Jennifer 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. Paul quickly went on to date actress Cameron Diaz. Vince Vaughn 
Photo: Michael Buckner/Getty Images Dated: June 2005 - December 2006 Jennifer and Vince Vaughn met during the filming of the movie The Breakup in Chicago and sparks quickly flew. It became difficult to tell the difference between romantic stills from the movie and candid photos of the two off set. A year into their romance, engagement rumors surfaced, but by December of that year, Jen and Vince were broken up for good. Brad Pitt 
Photo: Pascal Le Segretain/Getty Images Dated: November 1998 - June 2000 Married: July 2000 - October 2005 Jennifer Aniston and Brad Pitt were set up by their agents and hit it off. They readily admit that they practically moved in together after their first date. The two were engaged in December 1999 and tied the knot in July 2000 with a $1 million wedding. They invited 200 guests, had 50,000 flowers, a gospel choir, and fireworks at the reception. In January 2005, Jen and Brad separated amid very ugly rumors that Brad and his costar, Angelina Jolie, were having an illicit affair. By March, Jen and Brad filed for divorce and in October 2005 ended the marriage for good. Paul Rudd 
Photo: Bryan Bedder/Getty Images Dated: 1998 - 1999 Jennifer Aniston and the adorable Paul Rudd met during filming of The Object Of My Affection in 1998 and began a relationship that lasted about a year. Interestingly, Paul played the role of Jen's gay roommate/BFF in the film. Tate Donovan 
Photo: Vince Bucci/Getty Images Dated: 1995 - 1998 After ending a long term romance with actress Sandra Bullock, Tate Donovan hooked up with Jennifer Aniston. In 1998, after three years of dating, Jen and Tate became engaged. He even guest-starred as Jen's love interest on Friends for eight episodes in early 1998. The engagement only lasted a few months before they called it quits on the relationship. Adam Duritz 
Photo: Frederick M. Brown/Getty Images Briefly Dated: 1995 Jennifer Aniston dated Counting Crows singer Adam Duritz very briefly in 1995. What makes this relationship notable is the fact that soon after they split, Adam went on to date Courteney Cox, Jen's supposed BFF. Since Jen and Courteney still remain thick as thieves, they must have managed to get past it.   | |
Teen pop sensation 
Singer/actress 
Actress Alyssa Milano and her husband, agent David Bugliari, are the proud new parents of a baby boy. Alyssa, 38, gave birth to a son named Milo Thomas on the morning of August 30. The little man weighed in at 7 lbs. and measured 19 inches long. Happily married 
