Angelina Jolie Dating History: See All Her Exes and Former Husbands

She may have steered clear of romance lately, but Angelina Jolie’s dating history is full of some of Hollywood’s hottest stars. Before marrying Brad Pitt, she had her fair share of other high-profile relationships and rumored behind-the-scenes flings. She’s also been married not once, not twice, but three separate times. And though it may seem she’s 100 percent focused on being a mom these days, she has still made time for the occasional date.

The Maleficent actress is legally single, but she has yet to finalize her divorce with Brad. After a five-year legal battle, Brad was awarded joint custody of their six kids, In Touch confirmed on May 26. The former power couple share children Maddox, Pax, Zahara, Shiloh as well as twins Knox and Vivienne.

Although the ruling is temporary, the Salt star filed a request on May 21 with the Los Angeles Superior Court to modify Judge Ouderkirk’s order. Brad’s legal team “does not take issue” with his ex’s “right to contest” the latest custody ruling, but said, “This is not the time nor the place to do so,” adding the “appropriate time” would be after their private judge John W. Ouderkirk‘s decision becomes final.

However, things have been delayed yet again. On July 23, the California appeals court sided with Angelina and ruled Judge Ouderkirk should be disqualified. The 2nd District Court of Appeal agreed with her filing that the judge didn’t sufficiently disclose business relationships with Brad’s attorneys.

A representative for the Fight Club actor told CNN at the time that the appeals court decision was based on “a technical procedural issue.”

After the divorce drama, it seems Angelina has no plans to walk down the aisle again in the near future. The humanitarian joked about being single while appearing on the May 10 episode of E! News’ Daily Pop. “I probably have a very long list [of ‘no-nos’]. I’ve been alone for a long time now,” she shared in a rare update about her love life.

Angelina filed for divorce from the Once Upon a Time … In Hollywood actor after two years of marriage in September 2016, citing irreconcilable differences.

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“She’s always present with the kids and makes them all her priority,” an insider previously told In Touch about how she is trying to move forward in a positive direction. “Angelina knows she’s painted as the bad guy in her divorce [from Brad], but few people know that she’s struggled with the decisions she’s had to make. She wants it to be over just as much.”

Check out the gallery below to see Angelina Jolie’s dating history.

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Jonny Lee Miller

Angie met her first husband on the set of their 1995 film, Hackers. Though they initially kept their relationship casual — and open — they later tied the knot in March 1996. And the actress’ wedding attire wasn’t exactly traditional. She even said her I do’s in black rubber pants and a white shirt with her new husband’s name written on it in her own blood. “It’s your husband,” she joked with the New York Times in August 1996. ”You’re about to marry him. You can sacrifice a little to make it really special.” Though they split in 1997 and finalized their divorce in 1999, they stayed friends.

Jenny Shimizu

Before she and Jonny walked down the aisle, she was also dating Jenny, her Foxfire costar. In an interview with Girlfriends magazine, she gushed, “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.” Their relationship was cut short when she reunited with Jonny.

Mick Jagger

The Girl, Interrupted actress was also allegedly pursued by the Rolling Stones singer. They met when Angelina was hired for the “Anybody Seen My Baby” music video, and biographer Christopher Andersen says the rocker set his sights on her immediately. “She scares me a little — I like that,” he reportedly said.

Billy Bob Thornton

On the set of the 1999 movie Pushing Tin, Angie met her second husband. Though he was engaged to Laura Dern at the time, the two hit it off and Billy Bob called off his wedding. A year later, he and Angelina tied the knot. The pair even famously wore vials of each other’s blood, but their relationship wasn’t meant to last. Fortunately, the actress also managed to stay close with her second husband.

“We’ve been friends for years and years and years,” the Bad News Bears actor told Us Weekly in 2019. “We keep up with each other. She’s not in town a lot, so we don’t see each other much, but we talk.”

Val Kilmer

Another Alexander romance? Angelina’s on-screen husband clearly fell for her, but it’s not clear if they actually dated following filming on the 2004 movie. “I couldn’t wait to kiss Angie, buy her [a] Gulfstream jet and have V+J painted in rainbow glory on the trail,” he wrote in his 2020 memoir, I’m Your Huckleberry. “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.”

Brad Pitt

Then came the whirlwind that was Brangelina as the bad girl of Hollywood reportedly stole her Mr. and Mrs. Smith costar away from his then-wife, Jennifer Aniston. By October 2005, just a few months after their movie came out, the couple had already become parents together when Brad adopted Angie’s two children, Maddox and Zahara. Over the years, their family grew to include six kids after they adopted Pax and had Shiloh and twins Knox and Vivienne. Two years after their August 2014 wedding, they called it quits, and the rest — as they say — is history.

Jonny Lee Miller … Again?

As custody drama continues with Angie’s ex-husband Brad, could she be reuniting with her first ex-hubby, Jonny? In June 2021, Angelina was spotted at her Hackers costar’s Brooklyn apartment during a trip she took to New York City with her children. She arrived at the apartment alone, with a bottle of Peter Michael wine in hand.

In October, the pair were spotted again having dinner in Beverly Hills; the former married couple even drove off together, with Angelina on the passenger side.