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.”

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!

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