Angelina Jolie's Dating History: From Billy Bob Thornton to Brad Pitt

Angelina Jolie shares six children with ex Brad Pitt — though she filed for divorce in 2016 after two years of marriage

Angelina Jolie has had many high-profile relationships in her life, but these days she's focused on her children.

After filing for divorce from her longtime partner Brad Pitt in 2016, the actress told PEOPLE exclusively in 2017 that she was "a little bit stronger" following the split. "We all have our difficult times, but as a mother you also have a responsibility first and foremost towards the kids," she said. "They are going through their formative years and everything else comes second to that."

While fans often speculate about who Jolie may be dating, a source told PEOPLE in 2018 that she wasn't interested in making romantic connections at the time. "She isn't dating anyone and won't be for a very long time. She is focused on her children and their needs," the source said.

Prior to her relationship with Pitt, the actress was also married to her Pushing Tin costar Billy Bob Thornton from 2000 to 2003. In 2021, she was briefly linked to The Weeknd.

Most recently, Jolie was spotted having lunch with British environmentalist David Mayer de Rothschild in March 2023. However, a source later told PEOPLE that their lunch outing was for business purposes.

Here's a look back at Angelina Jolie's dating history.

Jonny Lee Miller

Jolie met English actor Jonny Lee Miller while working on the 1995 film Hackers. The two got married in a very small civil ceremony in 1996, but separated only a year later when their busy schedules kept them apart. The Maleficent actress filed for divorce in 1999, which was finalized the same year.

Despite their split, Jolie has spoken fondly of Miller over the years. In 2003, she called him a "solid man and a solid friend." Two years later, she was even spotted dining with him in London. "There was quite a lot of laughing," an observer told PEOPLE at the time. "They were all clearly enjoying themselves. You could tell (she) and Jonny are still very good friends."

Jenny Shimizu

Jolie met her Foxfire costar Jenny Shimizu around the same time she met Miller. The pair spent a lot of time together in 1996, and Jolie reportedly told Girlfriends Magazine in 1997, per InStyle, that the model "could have been a deep love" for her. "I probably would have married Jenny Shimizu if I hadn't married my husband," she added. "I fell in love with her the first second I saw her."

Billy Bob Thornton

In 1999, Jolie met actor Billy Bob Thornton while filming Pushing Tin. The pair eloped the following year in Las Vegas, shortly after Thornton abruptly ended his engagement to actress Laura Dern.

Perhaps the most iconic moment of Jolie and Thornton's marriage came in 2001 when they were were spotted wearing vials of each other's blood. Jolie even got a tattoo of her then-husband's name on her left arm.

In 2002, the couple announced they were adopting son Maddox from Cambodia, with Jolie's dad, Jon Voight, sharing the happy news. "I'm a grandfather today," he proudly announced during an Oscar nominee luncheon. Thornton also had two children from previous relationships.

However, Jolie and Thornton filed for divorce the same year, and Jolie sought full custody of Maddox. The divorce was finalized in May 2003.

After their split, Jolie had the tattoo of Thornton's name removed from her arm and eventually replaced it with the coordinates of her kids and now ex-husband Pitt's birthplaces.

Despite ending their marriage, Jolie and Thornton only have good things to say about each other. In 2008, Thornton told PEOPLE that he still "loves" Jolie. "She is a wonderful person and one of my closest friends."

In 2018, he even said they'd "probably still be together" if not for their "different lifestyles." He explained, "Hers is a global lifestyle and mine is an agoraphobic lifestyle. There was a different path in life we wanted to take."

Thornton's son Harry James Thornton said Jolie "still sends [him] Christmas gifts every year." He told Entertainment Tonight in 2022, "I don't talk to her on the phone every day but every now and then we talk."

Val Kilmer

Jolie and Val Kilmer sparked romance speculation while working on their 2004 film Alexander, in which the pair played the feuding mother and father of Alexander the Great. While there's no evidence they dated at the time, Kilmer admitted he had a crush on Jolie in his 2020 memoir I'm Your Huckleberry.

"I couldn't wait to kiss Angie, buy her a Gulfstream jet and have a V+J painted in rainbow glory on the tail," Kilmer wrote. "She had recently adopted her first child, Maddox, and the paparazzi were obsessed with this postmodern Madonna, the perfect picture of unapproachable stardom and impossibly chic maternal instinct."

Kilmer admitted he went as far as to ask the director to add some flashback scenes where the on-screen couple were in love. "He didn't pick up on the humor," the actor wrote. "I tried to clarify. Finally, I just sighed. 'Oh, never mind. I just dig her, Oliver [Stone]. It would be nice if we had some flashbacks when they were in love and happy together.' "

Brad Pitt

Jolie met Pitt when they worked together on 2005's Mr. and Mrs. Smith. At the time, Pitt was married to Friends actress Jennifer Aniston, though the two announced their separation in January 2005. (Pitt and Aniston's divorce was finalized later that year.)

In July, Pitt accompanied Jolie to Ethiopia to adopt her second child, Zahara. By January, Jolie's children Zahara and Maddox changed their last names to Jolie-Pitt. The couple welcomed their third child, Shiloh, in May 2006.

After adopting son Pax in March 2007 and welcoming twins Knox and Vivienne in July 2008, the couple got engaged in 2012. "It is a promise for the future and their kids are very happy," Pitt's manager Cynthia Pett-Dante told PEOPLE at the time.

The pair got married on Aug. 23, 2014. Pax baked their cake and walked Jolie down the aisle with Maddox. Zahara and Vivienne served as flower girls while Knox and Shiloh were ring bearers. "It was such a special day to share with our children and a very happy time for our family," the pair told PEOPLE.

However, Jolie filed for divorce from her husband two years later and requested custody of the kids with visitation rights for Pitt. "This decision was made for the health of the family," Jolie's attorney told PEOPLE, following an incident on a private flight.

In another statement to PEOPLE, Pitt said, "I am very saddened by this, but what matters most now is the well being of our kids. I kindly ask the press to give them the space they deserve during this challenging time."

The divorce began a long custody battle. While he was originally awarded more time with the children in May 2021, Pitt lost it two months later when their judge was removed from the case for not disclosing his business relationship with him.

In 2022, Pitt sued Jolie for selling her stake in the winery they purchased together, and in August Jolie requested the FBI documents from their airplane incident be made public.

"What are the motivations of a person to take up court time and public resources in filing an anonymous FOIA request for material they have had for years?" a source close to Pitt told PEOPLE. "There's only one: to inflict the most amount of pain on her ex. There is no benefit to this. It is harmful to the children and the entire family for this to be made public."

The Weeknd

Jolie and The Weeknd sparked romance rumors in 2021 when they were spotted sharing not one but two dinners out together.

A source told PEOPLE the couple had known each other "for some time" and shared a bond over their connection to Ethiopia — the R&B crooner had partnered with the World Food Program US to donate $1 million in relief efforts in the country, while Jolie adopted her daughter and launched The Zahara Program to help girls there.

The "Blinding Lights" singer further fueled the speculation with the release of his song "Here We Go... Again" in January 2022, which included the line: "My new girl, she a movie star." However, neither party ever commented on the rumors, and The Weeknd was spotted kissing DJ Simi Khadra one month later.

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