Angelina Jolie’s Dating History: From Billy Bob Thornton to Brad Pitt, Rumored To Be With The Weeknd

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

Although Angelina Jolie has been in a number of well-known relationships, her current priorities are her kids.

The actress revealed exclusively to PEOPLE in 2017 that she was “a little bit stronger” after divorcing her longtime lover Brad Pitt in 2016. “We all have our difficult times, but as a mother you also have a responsibility first and foremost towards the kids,” she stated. “They are going through their formative years and everything else comes second to that.”

Although fans frequently conjecture about Jolie’s potential partner, an insider informed PEOPLE in 2018 that she had no interest in dating at the time. “She has no current romantic partner and won’t for a very long time. The insider stated that she is preoccupied with her kids and their demands.

The actress was previously married to Billy Bob Thornton, who she costarred with on Pushing Tin, from 2000 until 2003, before her union with Pitt. She had a brief connection to The Weeknd in 2021.

The last time Jolie was seen out and about was in March 2023, eating lunch with British environmentalist David Mayer de Rothschild. But afterward, PEOPLE was informed by a source that the lunch outing was for business.

This is a look into Angelina Jolie’s past relationships.

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.

Jenny Shimizu

Around the same time that Jolie met Miller, she also met Jenny Shimizu, her costar in Foxfire. The couple apparently spent a lot of time together in 1996. According to InStyle, Jolie claimed in 1997 that the model “may have been a deep love” for her, as reported by Girlfriends Magazine. “I probably would have married Jenny Shimizu if I hadn’t married my husband,” she stated. “I fell in love with her the first second I saw her.”

Billy Bob Thornton

While filming Pushing Tin in 1999, Jolie got to know actor Billy Bob Thornton. The next year, just after Thornton called off his engagement to actress Laura Dern, the couple eloped in Las Vegas.

The sight of Jolie and Thornton wearing vials containing each other’s blood in 2001 may have been the most memorable event of their marriage. Jolie even had the name of her ex-husband permanently inked on her left arm. When the couple revealed in 2002 that they were adopting a son named Maddox from Cambodia, Jon Voight, Jolie’s father, shared the good news. He declared with pride, “I’m a grandfather today,” during a luncheon for Oscar nominees. In addition, Thornton had two kids from past relationships.

But the following year, Jolie and Thornton filed for divorce, with Jolie requesting sole custody.

Val Kilmer

While filming Alexander in 2004, Jolie and Val Kilmer aroused rumors of a romance between them as they portrayed Alexander the Great’s rival parents. In his 2020 memoir I’m Your Huckleberry, Kilmer said that he had a crush on Jolie, even though there is no proof that they dated at the time.

“I couldn’t wait to kiss Angie, buy her a Gulfstream jet and have a V+J painted in rainbow glory on the tail,” wrote Kilmer. “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.”

While filming Alexander in 2004, Jolie and Val Kilmer aroused rumors of a romance between them as they portrayed Alexander the Great’s rival parents. In his 2020 memoir I’m Your Huckleberry, Kilmer said that he had a crush on Jolie, even though there is no proof that they dated at the time.

“I couldn’t wait to kiss Angie, buy her a Gulfstream jet and have a V+J painted in rainbow glory on the tail,” wrote Kilmer. “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 and Pitt first collaborated on the 2005 film Mr. and Mrs. Smith. Pitt was wed to Jennifer Aniston, an actress from Friends, at the time; nevertheless, the couple separated in January 2005. (Later that year, Pitt and Aniston’s divorce was officially formalized.)

Pitt traveled to Ethiopia with Jolie in July to adopt Zahara, her second child. Zahara and Maddox, Jolie’s kids, changed their last names to Jolie-Pitt by January. In May 2006, the couple welcomed Shiloh as their third child.

The couple were engaged in 2012 after welcoming twins Knox and Vivienne in July 2008 and adopting a baby named Pax in March 2007. “It is a promise for the future and their kids are very happy,” Cynthia Pett-Dante, Pitt’s manager, said at the time to PEOPLE.

The couple wed on August 23, 2014. While Maddox escorted Jolie down the aisle, Pax made their cake. Knox and Shiloh carried the rings, and Zahara and Vivienne were flower girls. “It was such a special day to share with our children and a very happy time for our family,” both of them told PEOPLE.

But two years later, Jolie filed for divorce from her husband, asking for joint custody of the children as well as Pitt’s visitation rights. After an incident on a private jet, Jolie’s lawyer told PEOPLE, “This decision was made for the health of the family.”

Pitt stated, “I am very saddened by this, but what matters most now is the well-being of our kids,” in a different statement to PEOPLE. I respectfully request that the media allow them the room they need during this trying time.”

The divorce sparked a protracted custody dispute. Pitt first won additional time with the kids in May 2021, but that was short-lived as their judge was ousted from the case two months later for failing to disclose Pitt’s business relationship with the children.

Pitt filed a lawsuit against Jolie in 2022 for selling her share of the winery they jointly bought, and in August, Jolie asked for the release of the FBI files pertaining to their plane incident.

The Weeknd

When Jolie and The Weeknd were seen out together for two dinners in 2021, romance speculations began to circulate.

The R&B singer and World Food Program US partnered to donate $1 million for relief efforts in Ethiopia, and Jolie adopted her daughter and started The Zahara Program to support girls there. According to a source who spoke to PEOPLE, the couple had known each other “for some time” and were drawn to each other because of their shared ties to the country.

The singer of “Blinding Lights” added fuel to the rumors when his song “Here We Go… Again” was released in January 2022 and featured the phrase, “My new girl, she a movie star.” But none of the parties addressed the rumors, and DJ Simi Khadra was seen kissing The Weeknd.