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Brad Pitt and Angelina Jolie attend the Inglourious Basterds Premiere held at the Palais Des Festivals during the 62nd International Cannes Film Festival on May 20th, 2009 in Cannes, France© Getty Images

Angelina Jolie's very public romantic history: from Jonny Lee Miller to Brad Pitt

The Maleficent star shares her six children with one of her ex-husbands

Ahad Sanwari
Ahad Sanwari - New York
Senior WriterNew York
March 4, 2024
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Angelina Jolie reigns supreme as one of the most magnetic stars in Hollywood, having occupied a space in the public consciousness for over four decades.

Alongside her celebrated film career and humanitarian work, however, her love life has been the subject of much coverage and speculation, given her relationships with some of the industry's leading men.

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Here's a rundown of Angelina's most high-profile public relationships, from her three marriages to her on-set romances…

Teen Love

Angelina, now 48, has spoken about her boyfriend as a teenager when she was 14, which she'd compared to a "marriage" in an interview with the Calgary Sun.

LOS ANGELES - 1991: Actress Angelina Jolie poses for a portrait in 1991 in Los Angeles, California.© Getty Images
Angelina's first serious relationship was with her teenage boyfriend, which lasted for two years

In fact, her boyfriend had moved with her into her mother Marcheline Bertrand's home, where they remained for two years. 

"We were together and serious for two years," she remarked. "That relationship felt like a marriage. It was a tough breakup, so I immersed myself in acting to get over it."

Jonny Lee Miller

In 1995, Angelina embarked on her first relationship since her teenage breakup when she entered a romance with her Hackers co-star, English actor Jonny Lee Miller.

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Jonny Lee Miller and Angelina Jolie in a scene from the film 'Hackers', 1995.© Getty Images
She married her "Hackers" co-star Jonny Lee Miller in 1996 and they were divorced by 2000

After production on the film ended, they lost touch, but reconnected months later and tied the knot in 1996, and the actress famously showed up for their wedding in rubber pants and a white tee with the groom's name in blood. 

Sadly, their romance was not to last, and they separated a year and a half later. Their divorce was finalized in early 2000, but they remained friends after their separation.

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Jenny Shimizu

When she'd lost touch with Jonny, she entered into a relationship with American actress and model Jenny Shimizu, which began on the set of their 1996 movie FoxFire.

Model Jenny Shimizu attends the launch of NARS 15X15 a project to celebrate 15 years of NARS at Industria Superstudio on November 12, 2009 in New York City.© Getty Images
She intermittently dated her "FoxFire" co-star Jenny Shimizu

In a 1997 interview, she confirmed the romance, saying: "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… She's great. We had a lot of fun."

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Jenny claimed in a later interview that their relationship continued for years after, even during Angelina's marriages, which the actress never confirmed. However, she openly stated years later that she did in fact consider herself to be bisexual.

Timothy Hutton

Angelina Jolie and Timothy Hutton during Premiere "Playing God" at Criterion Theater in New York City, NY, United States.© Getty Images
She reportedly dated her "Playing God" co-star Timothy Hutton between 1997 and 1999

While less notable than her others, Angelina reportedly dated her Playing God (1997) co-star Timothy Hutton in 1996 while they were making the film, soon after her separation from Jonny.

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It's unclear how long their relationship lasted, however it apparently was ongoing when in 1999, she met…

Billy Bob Thornton

On the set of the movie Pushing Tin, Angelina met the American actor and filmmaker, although they didn't pursue a romance at the time due to her relationship with Timothy and his with actress Laura Dern.

Angelina Jolie and Billy Bob Thornton during "Gone in 60 Seconds" Los Angeles Premiere at National Theater in Westwood, California, United States.© Getty Images
In 2000, she married "Pushing Tin" co-star Billy Bob Thornton, though they were divorced by 2003

They soon got together and got married in 2000, with their public displays of affection receiving much attention, including the infamous wearing of the vials of each other's blood round their necks.

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They planned to adopt a child together from Cambodia in 2002, but abruptly separated three months later, and were divorced by 2003. Angelina went through with the adoption solo, welcoming son Maddox, now 22.

Brad Pitt

Angelina and Brad Pitt's legendary love story controversially began on the set of 2005's Mr and Mrs Smith, which was plagued with accusations of infidelity leading to Brad's divorce from Jennifer Aniston.

Brad Pitt and Jennifer Aniston first met in 1994, but didn't begin dating until 1998. They married in 1999, a year after Brad proposed to Jennifer. The couple announced their split in early 2005.© Getty Images
Angelina and Brad's relationship was believed to have resulted in the end of his marriage to Jennifer Aniston

Both actors have maintained that they never took that extra step, and kept coy about their relationship till January 2006, when she confirmed they were expecting their first child together, welcoming daughter Shiloh, now 17, later that year.

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They were dubbed "Brangelina" and became Hollywood's ultimate power couple, thanks to their joint A-list status, acclaimed work, and large family (they were the parents of six children while together, including two Angelina had adopted before Shiloh's birth).

Brad Pitt and Angelina Jolie arrive at the 84th Annual Academy Awards in 2012© Getty Images
The couple were famously married in 2014 and separated two years later

They announced their engagement in April 2012 and tied the knot twice in August 2014. However, they separated in 2016 and were declared legally single in 2019, although their divorce and division of joint properties has remained contentious ever since.

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