A Comprehensive Guide To Angelina Jolie's Complete Dating History (2024)

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 andMarcheline 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

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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

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Jolie reportedly fell head over heels for herFoxfirecostar, 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

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Another co-star, Billy Bob Thornton caught the attention of the actress when they filmed the 1999 comedy-dramaPushing 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 withEntertainment 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 toldUsMagazine in 2019 that they “remain good friends.”

Brad Pitt

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After filming the action flick 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 theirChâteau Miraval estate in France.

In September 2016, Jolie filed for divorce, citingirreconcilable 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

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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 toldUsin 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

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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…

Pema Bakshi

I'm an enthusiast with a profound understanding of celebrity relationships and the intricacies of the entertainment industry. Having closely followed Angelina Jolie's career and personal life, I can provide valuable insights into her dating history.

Angelina Jolie, born into Hollywood royalty as the daughter of Jon Voight and Marcheline Bertrand, has been a prominent figure in the industry since the 1990s. At the age of 14, she entered her first serious relationship, which her mother supported by allowing the boyfriend to live with them. Jolie defended her mother's decision, emphasizing that it kept her out of trouble and allowed her to continue her education.

Now, delving into Jolie's dating history:

  1. Johnny Lee Miller (1996-1999):

    • Jolie and Miller initially got together during the filming of "Hackers" in 1995.
    • They married in 1996 in a unique ceremony where Jolie wore black rubber pants and a white shirt with the groom's name written in blood.
    • The couple separated in 1997 due to busy schedules, officially divorcing in 1999.
  2. Jenny Shimizu (Briefly in 1997):

    • Jolie had a brief relationship with her "Foxfire" co-star Jenny Shimizu.
    • Jolie expressed that she might have married Shimizu if not for her reunion with Johnny Lee Miller.
  3. Billy Bob Thornton (2000-2003):

    • Jolie and Thornton, co-stars in "Pushing Tin," got married in 2000 during a trip to Las Vegas.
    • Known for wearing vials of each other's blood around their necks.
    • The couple announced their intention to adopt Maddox in 2002 but divorced a few months later.
  4. Brad Pitt (2005-2016):

    • Jolie and Pitt fell in love during the filming of "Mr. & Mrs. Smith" in 2005.
    • Adopted children together and had biological twins.
    • Married in 2014 and filed for divorce in 2016, currently finalizing the divorce and battling for custody of their six children.
  5. The Weeknd (2021):

    • Jolie was spotted with The Weeknd in July 2021, sparking dating rumors.
    • The Weeknd's lyrics in his album hinted at a romantic connection.
    • Their current relationship status is unclear.
  6. Paul Mescal (Rumors in 2023):

    • Recent rumors suggest a connection between Jolie and actor Paul Mescal, known for "Normal People."
    • Sightings and photographs of them together have fueled speculation, although the nature of their relationship remains unconfirmed.

Intriguingly, Jolie's dating history reflects a mix of on-screen and off-screen romances, with each relationship having its unique dynamics and public attention. The twists and turns of her personal life continue to captivate audiences, making her an enduring figure in the world of celebrity relationships.

A Comprehensive Guide To Angelina Jolie's Complete Dating History (2024)

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