A Comprehensive Guide To Angelina Jolie’s Complete Dating History

She's had some A-list admirers.

Since her ascension to fame in the ’90s, Angelina Jolie has been at the centre of attention. And being one of the most formidable women in the business, it’s no surprise her love life continues to fascinate us.

Born and raised in Hollywood to famous parents, Jon Voight and Marcheline Bertrand, the actress revealed she had her first serious boyfriend at the age of 14, so serious that he actually lived with her and her family. 

In a 2003 interview with Cosmopolitan, Jolie defended her mother’s tolerance of the situation. “My mother is so caring and nurturing, and the choices she made for me were not irresponsible,” she said. “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.”

Two years on, though, she ended things to focus on her budding career, but it certainly wouldn’t be her last serious relationship. With three marriages and six kids, Jolie’s dating history has been filled with whirlwind romances, co-star connections and plenty of rumours. Ahead, we chart the actress’ entire dating history.

Johnny Lee Miller

Angelina Jolie and Johnny Lee Miller
Angelina Jolie and Johnny Lee Miller (Credit: Getty Images)

After initially getting together during the filming of Hackers in 1995, Angelina Jolie and Johnny Lee Miller parted ways before come back together and getting hitched in 1996. The civil ceremony was attended by only her mother and his best friend. The eccentric bride eschewed the traditional white gown for black rubber pants with a white shirt that had the groom’s name written in blood on the back—a task that she told The New York Times that she handled “very carefully” with “a clean surgical needle.”

In 1997, the couple separated due to their busy schedules keeping them apart, officially divorcing in 1999. Jolie told Buzzfeed in 2014 that Miller is “still a great friend.” Last June the two even sparked rumours of a rekindling when Jolie was photographed arriving at her ex-husband’s Brooklyn apartment one night with a bottle of wine. 

Jenny Shimizu

Angelina Jolie and Jenny Shimizu
Angelina Jolie and Jenny Shimizu

Jolie reportedly fell head over heels for her Foxfire costar, whom she dated briefly before getting back together with Miller.

In an interview with Girlfriends magazine in 1997, the actress confessed that it likely would’ve gone a lot further had she not rekindled with Miller. “I probably would have married Jenny Shimizu if I hadn’t married my husband,” she said, adding that the spark was instant. “I fell in love with her the first second I saw her.”

Billy Bob Thornton

Angelina Jolie and Billy Bob Thornton
Angelina Jolie and Billy Bob Thornton (Credit: Getty Images)

Another co-star, Billy Bob Thornton caught the attention of the actress when they filmed the 1999 comedy-drama Pushing Tin. Playing an on-screen married couple, the two ended up becoming husband and wife in real life during a trip to Las Vegas in 2000.

Awkwardly, the actor was reportedly still engaged to actress Laura Dern at the time. In an interview with Talk magazine that same year, Dern said “While I was away, my boyfriend got married, and I’ve never heard from him again.”

But that wasn’t even the most newsworthy part about the coupling. Their tendency to don vials of each other’s blood around their necks—an act Jolie once referred to as “a sweet gesture” in a 2008 interview with Entertainment Weekly—still raises eyebrows to this day.

The pair announced their intention to adopt seven-month-old Maddox together in 2002, but they split just a few months later. Jolie went ahead with completing the adoption process on her own.

Their divorce was finalised in 2003, however, Thornton told Us Magazine in 2019 that they “remain good friends.”

Brad Pitt

Angelina Jolie and Brad Pitt
Angelina Jolie and Brad Pitt (Credit: Getty Images)

After filming the action flick Mr. & Mrs. Smith together in 2005, Jolie and her co-star Brad Pitt fell in love on set. While Pitt was still married to Jennifer Aniston at the time, the two have vehemently denied any physical affairs. Jolie once said on the Today show, “I wouldn’t be attracted to a man who would cheat on his wife.”

The pair got real serious real quick, with Jolie falling pregnant with their first child, Shiloh, by the end of 2005. 

Pitt legally adopted Maddox and the two both adopted Zahara in 2006 and Pax in 2008, the same year that the actress gave birth to twins Knox and Vivienne. Nine years later, the couple finally wed at their Château Miraval estate in France.

In September 2016, Jolie filed for divorce, citing irreconcilable differences and requested physical custody of all their six children with visitation for Pitt. The two are still finalising their divorce as they continue to battle for custody of their children. 

The Weeknd

Angelina Jolie and The Weeknd
The Weeknd (Credit: Getty Images)

In July of 2021, the actress took us by surprise when she was spotted dining with The Weeknd. Following a series of dinners and concert dates with the musician—real name Abel Tesfaye—’sources’ began to confirm the two were an item. “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-winning actress.

The Weeknd fuelled suspicions when songs in his album included lyrics like “My new girl, she a movie star” repeated throughout. 

The two have since not been since publicly together, and Tesfaye has been connected to his The Idol co-star Lily-Rose Depp.

Paul Mescal

Angelina Jolie and Paul Mescal
Paul Mescal (Credit: Getty Images)

As of 2023, Paul Mescal and Angelina Jolie might just be the latest unlikely coupling.

Despite the Normal People‘s engagement to Phoebe Bridgers only recently confirmed, rumours of their split quickly circulated following sightings of the Bridgers with comedian Bo Burnham. Following the sightings, more rumours began swirling about Mescal being seen with Angelina Jolie. 

In early January, the two were even photographed getting coffee with Jolie’s daughter, Shiloh after the two watched his performance in A Streetcar Named Desire. While it’s unconfirmed if the two are romantically involved, the sightings are certainly enough to get tongues wagging. We say watch this space…

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