Aniston has previously dated musician Adam Duritz, and was engaged to actor Tate Donovan. Her high-profile relationship with actor Brad Pitt was frequently publicized in the press. She married Pitt on July 29, 2000, in a lavish Malibu wedding. For years their marriage was considered the rare Hollywood success. However, when Pitt showed up to the Ocean's Twelve premiere without Aniston, rumors that their relationship was on the rocks began. In early January 2005, the couple was seen vacationing in the Caribbean with her Friends co-star Courteney Cox and her husband, actor David Arquette, and photos on the beach showed them kissing and affectionate. On January 7, 2005 they announced their separation.
Rumors that Pitt had fallen for actress Angelina Jolie began when they were shooting the film Mr. and Mrs. Smith. Jolie and Pitt both denied any claims of adultery, with Jolie declaring in an interview in 2005, "To be intimate with a married man, when my own father cheated on my mother, is not something I could forgive. I could not look at myself in the morning if I did that. I wouldn't be attracted to a man who would cheat on his wife." Pitt and Aniston were seen together publicly after announcing their separation, even at a dinner party for Aniston's thirty-sixth birthday in February, and friends of the couple had declared they were reconciling. Aniston, however, filed for divorce on March 25, 2005. A divorce was finalized on October 2, 2005.
Media reports speculated that the split was due to Aniston's refusal to have children with him; t-shirts were sold after their separation with the phrase "I'll Have Your Baby, Brad!". Aniston denied that this was the cause of their split in an August 2005 Vanity Fair interview, stating, "...I've always wanted to have children, and I would never again give up that experience for a career." Aniston also revealed that her divorce prompted her to reach out to her mother, from whom she was estranged for nearly a decade. They initially became estranged when Nancy talked about her daughter on a television show and later wrote a book titled From Mother and Daughter to Friends: A Memoir (1999).
She has also stated that she was devastated by the death of her longtime therapist, whose work helped to make the separation from Pitt easier. Aniston has said that her relationship with Pitt, which she does not regret, was "seven very intense years together" and that "it was a beautiful, complicated relationship." Since the couple's divorce, Aniston has been romantically linked to actor Vince Vaughn, British model Paul Sculfor and singer John Mayer.
In August 2006, Aniston denied rumors that she was engaged to Vaughn or that the actor had proposed. In October 2006, gossip magazine Us Weekly quoted sources from Vaughn that the couple had broken up. In December 2006, representatives for both Aniston and Vaughn confirmed that they had indeed split up a few weeks before when Aniston visited Vaughn in London.
The intense media scrutiny of Aniston's private life continued. It was reported in April 2008 that singer John Mayer and Aniston were an item. A few weeks later, Mayer hinted the rumours were true when he told reporters "listen, this is not a scandal, this is not an issue, this is not a problem, this needs no spin control."
On August 13, 2008, the UK's Daily Mirror reported that Aniston was "dumped" by Mayer after the pair initially decided to spend some time apart before making the break official earlier this week. However, according to USmagazine.com, reports that Mayer had dumped Aniston were not true and that it was she who dumped him. A relationship expert tells USmagazine.com that Mayer's pride and ego was the reason he has been telling people he dumped Aniston. Rumors were put to rest when Mayer explained on his Myspace that he had ended the relationship because "[he doesn't] want to waste somebody's time if something's not right". On October 11, 2008, Mayer and Aniston reunited for a dinner at romantic restaurant, Il Mulino. Since then, Aniston and Mayer have been reported to reunite quite a few times, once to celebrate Mayer's 31st birthday. She has since confirmed on Oprah, she is again dating John Mayer.
