Angelina Jolie's Love Life Explained: What Went Wrong — From Billy Bob Thornton to Brad Pitt and More

Jonny Lee Miller

Angelina Jolie 's first known relationship and first marriage was to Jonny Lee Miller . They met on the set of their 1995 film Hackers and tied the knot in a civil ceremony the following year.

Due to their busy schedules, Jolie and Miller called it quits in 1997. The Maleficent actress filed for divorce in 1999 and had it finalized later that year.

Despite their split, Jolie revealed in her interviews that she has remained friends with her ex-husband.

Jenny Shimizu

In 1997, the mom-of-six admitted to Girlfriends magazine that she fell in love with her Foxfire costar Jenny Shimizu — who has since married Michelle Harper — before her wedding to Miller.

"I probably would have married [Jenny Shimizu] if I hadn't married my husband," she added. "I fell in love with her the first second I saw her."

Billy Bob Thornton

The 48-year-old Eternals actress met Billy Bob Thornton while filming Pushing Tin in 1999. They exchanged their vows the following year in Las Vegas and adopted Maddox Jolie-Pitt in 2002.

However, Angelina and Billy Bob filed for divorce the same year and finalized it in 2003.

Val Kilmer

Months after Angelina's divorce from Billy Bob was finalized, she worked with Val Kilmer in Alexander . The pair never confirmed their relationship, but the Batman Forever star wrote in his 2020 memoir I'm Your Huckleberry that he admired Angelina.

"I couldn't wait to kiss Angie, buy her a Gulfstream jet and have a V+J painted in rainbow glory on the tail," Val wrote.

Brad Pitt

Angelina moved on with her Mr. and Mrs. Smith costar, Brad Pitt , while he was still married to Jennifer Aniston . They began dating after his divorce from the Friends actress, and they adopted Angelina’s second child, Zahara Jolie-Pitt , in July 2005.

They later added Jolie-Pitt to Maddox and Zahara's names.

In the years thereafter, they welcomed Shiloh Jolie-Pitt , Pax Jolie-Pitt , Knox Jolie-Pitt and Vivienne Marcheline Jolie . The latter child has dropped Pitt from her last name.

The pair finally tied the knot on August 23, 2014, after nine years of dating. However, the Lara Croft: Tomb Raider actress filed for divorce from Brad two years later and requested custody of their children .

The end of their relationship became the beginning of their lengthy divorce and custody battle. They have also been suing each other over their winery .

The Weeknd

In 2021, Angelina sparked dating rumors with The Weeknd after they were spotted having dinners and attending concerts together .

"Ange has been in contact with Abel for a while, he was in New York at the same time as her and the kids," a source told The Sun . "They met up for lunch in private. She took Pax along because he's a big fan and they got along really well, he was obviously thrilled. They are just friends, but who knows it could be more in the future, he's made no secret of the fact he has a huge crush on her."

However, the buzz stopped after The Weeknd was pictured kissing Simi Khadra in 2022.