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Jolie had a serious boyfriend for two years from the age of 14. They lived together in her mother's home, of which she has said, "He was my first boyfriend at a time when I wanted to be promiscuous and was starting to be sexual. We were in my bedroom, in my environment, where I was most comfortable and I wasn't in danger." She later compared the relationship to a marriage in its emotional intensity, and said that the breakup compelled her to dedicate herself to her acting career at the age of 16.|
During filming of Hackers (1995), Jolie had a romance with British actor Jonny Lee Miller, her first lover since the relationship in her early teens. They were not in touch for many months after production ended, but eventually reconnected and married soon after on March 28, 1996. She attended her wedding in black rubber pants and a white T-shirt, upon which she had written the groom's name in her blood. Jolie and Miller separated in September 1997 and divorced on February 3, 1999. They remained on good terms, and Jolie later explained, "It comes down to timing. I think he's the greatest husband a girl could ask for. I'll always love him, we were simply too young."
Jolie had a brief relationship with model-actress Jenny Shimizu on the set of Foxfire (1996). She later said, "I would probably have married Jenny if I hadn't married my husband. I fell in love with her the first second I saw her." Shimizu claimed in 2005 that her relationship with Jolie had lasted many years and continued even while Jolie was romantically involved with other people. In 2003, asked if she was bisexual, Jolie responded, "Of course. If I fell in love with a woman tomorrow, would I feel that it's okay to want to kiss and touch her? If I fell in love with her? Absolutely! Yes!"
After a two-month courtship, Jolie married actor Billy Bob Thornton on May 5, 2000, in Las Vegas. They met on the set of Pushing Tin (1999), but did not pursue a relationship at that time as Thornton was engaged to actress Laura Dern. As a result of their frequent public declarations of passion and gestures of love—most famously wearing one another's blood in vials around their necks—their marriage became a favorite topic of the entertainment media. Jolie and Thornton announced the adoption of a son from Cambodia in March 2002, but abruptly separated three months later. Their divorce was finalized on May 27, 2003. Asked about the sudden dissolution of their marriage, Jolie stated, "It took me by surprise, too, because overnight, we totally changed. I think one day we had just nothing in common. And it's scary but... I think it can happen when you get involved and you don't know yourself yet."
In early 2005, Jolie was involved in a well-publicized Hollywood scandal when she was accused of being the reason for the divorce of actors Brad Pitt and Jennifer Aniston. She and Pitt were alleged to have started an affair during filming of Mr. & Mrs. Smith (2005). She denied this on several occasions, but later admitted that they "fell in love" on the set. She explained 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." Jolie and Pitt did not publicly comment on the nature of their relationship until January 2006, when Jolie confirmed to People that she was pregnant with Pitt's child. The couple—dubbed "Brangelina" by the entertainment media—are the subject of worldwide media coverage.