Angelina Jolie’s Dating History: Brad Pitt, Billy Bob Thornton and More

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Angelina Jolie’s Dating History: Brad Pitt, Billy Bob Thornton and More

Angie’s admirers! Angelina Jolie has only been in five serious relationships, but her love life has been the center of attention since her film career took off in the 1990s. The Oscar winner got her first boyfriend in the late ‘80s at the age of 14. While she never publicly disclosed his identity, their relationship was so significant that her mother, Marcheline Bertrand, let him live in their house, an unconventional arrangement that Jolie defended years later. “My mother is so caring and nurturing, and the choices she made for me were not irresponsible,” she told Cosmopolitan in 2003. “When I was 14, I was either going to be reckless on the streets with my boyfriend or he was going to be with me in my bedroom with my mom in the next room because I was going to have a boyfriend. She made the choice, and because of it, I continued to go to school every morning and explored my first relationship in a safe way. So in some strange way, she really did the right thing. It kept me out of trouble.” Jolie dated her teenage sweetheart for two years, telling The Sun in 2011 that they “lived like a married couple.” However, after she turned 16, she ended their romance to focus on her budding acting career. It was not until 1994 that the Los Angeles native found love again. While filming the 1995 crime flick Hackers, she entered into a relationship with her costar Jonny Lee Miller. They lost touch after production wrapped, and she subsequently began seeing her Foxfire costar Jenny Shimizu. “It had never crossed my mind that I was going to one day experiment with or kiss a woman, it was never something I was looking for,” Jolie, who later came out as bisexual, told Rolling Stone in 2001. “I just happened to fall for a girl.” [jwplayer o31hUC4A-l3ahXupL] After the Gia star’s flame with Shimizu fizzled out, she reconnected with Miller. They eloped in 1996, only to divorce three years later. “I wasn’t even a good friend because I was just absent,” she recalled to Rolling Stone of the final days of her and Miller’s union. “I’d go for drives and disappear or go film something and be in hotels forever and not do anything, not have friends, not visit, not hang out. I couldn’t calm down and just live life.” Jolie shocked the world in 2000 when she married again, this time to Billy Bob Thornton. Their marriage did not last long, however, as they abruptly split in 2002 and finalized their divorce the following year. “It took me by surprise too because overnight, we totally changed,” she admitted to Vogue in 2004. “Because we’re actors, we go away for months at a time and you grow and change separately. 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. It’s taken me a while to grow up, and I still think I’m not even close to it yet. So I’ve kind of had to check myself: Don’t even consider a relationship for another seven, eight years.” The Tomb Raider star broke her promise to herself in 2004 when she fell for another costar, Brad Pitt, on the set of Mr. & Mrs. Smith. He was married to Jennifer Aniston at the time, a scandal that rocked Hollywood. Us Weekly broke the news of Jolie and Pitt’s romance in 2005 with a photo of them on Diani Beach in Kenya with her then-3-year-old son, Maddox, whom she adopted from Cambodia in 2002. Brangelina, as they became known, adopted twice more, Zahara from Ethiopia in 2005 and Pax from Vietnam in 2007, and welcomed three biological children: Shiloh in 2006 and twins Knox and Vivienne in 2008. They quietly married in 2014 with their children among those on the small guest list. Jolie filed for divorce in 2018, and they became legally single in 2019. “I separated for the well-being of my family,” the Maleficent star told Vogue India in 2020. “It was the right decision. I continue to focus on [the children’s] healing.” Scroll down for more details on Jolie’s high-profile relationships! [podcast_block]

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Jonny Lee Miller

Nearly two years after filming Hackers together, Jolie tied the knot with Miller in 1996 in a civil ceremony attended by only her mom and his best friend. The bride wore black rubber pants and a white shirt with the groom’s name written in blood on the back. (She later told The New York Times that she “very carefully” drew the blood herself using “a clean surgical needle.”) The couple’s busy schedules kept them apart, and they separated in 1997. She filed for divorce in 1999, and the case was finalized later that year. Jolie told BuzzFeed in 2014 that Miller is “still a great friend.”

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Jenny Shimizu

Jolie fell head over heels for her Foxfire costar, whom she romanced shortly before rushing to the altar with Miller. “I probably would have married Jenny Shimizu if I hadn’t married my husband. I fell in love with her the first second I saw her,” she told Girlfriends magazine in 1997.

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Billy Bob Thornton

Jolie met Thornton on the set of the 1999 comedy-drama Pushing Tin, in which they played a married couple. They secretly became husband and wife in real life in 2000 during a trip to Las Vegas. The actor was still engaged to Laura Dern at the time. (“While I was away, my boyfriend got married, and I’ve never heard from him again,” Dern claimed to Talk magazine later that year.) Jolie and Thornton raised eyebrows in 2001 when they started wearing necklaces filled with each other’s blood, which she called “a sweet gesture” in a 2008 interview with Entertainment Weekly. The pair announced their intention to adopt Maddox together in 2002, but they split months later and Jolie moved forward with the process on her own. They finalized their divorce in 2003. Thornton exclusively told Us in 2019 that he and Jolie remain “good friends.”

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Brad Pitt

Jolie was accused of causing Pitt’s divorce from Aniston in 2005 when the Mr. & Mrs. Smith costars fell in love on set. However, the Girl, Interrupted star denied they had a physical affair, saying on the Today show that year, “I wouldn’t be attracted to a man who would cheat on his wife.” That said, Brangelina’s romance soon went full steam ahead. She became pregnant with their first child together, Shiloh, by the end of 2005. Pitt legally became Maddox and Zahara’s father in 2006, and he adopted Pax in 2008, the same year that Jolie gave birth to Knox and Vivienne. Now a family of eight, the By the Sea costars announced their engagement in 2012. They wed at their Château Miraval estate in France two years later. Jolie filed for divorce in 2016. She and Pitt have yet to finalize their divorce as they battle for custody of their kids.

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The Weeknd

The actress was first spotted with the musician in July 2021, sparking romance rumors after the duo were seen on a series of dinner and concert dates. “Both Angie and Abel are telling people that they are just friends, but those who know them think something romantic is going on,” a source exclusively told Us in September 2021, noting that The Weeknd “is in awe of” the Oscar winner. Jolie, for her part, has remained coy about the nature of her relationship with the “Blinding Lights” singer.