by Delilah Gray
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While Angelina Jolie is known for being a generous soul with her years of charity work and her iconic movie roles, she’s also known for having one of the most controversial dating timelines in Hollywood.
From multiple on set-romances and an elopement to blood necklaces and even bloodier wedding outfits, you name it, and Jolie’s dating life probably has it. Not only did she find herself in hot water after her controversial marriages to Billy Bob Thornton and later Brad Pitt.
Now, when you’re as big as Jolie, there are going to be a lot of rumors. Not only has she been linked to stars like Lady Gaga and Colin Farrell, but the rumors turned up after her divorce from Pitt. In 2021 and 2023, people were convinced something was going on between her and The Weeknd, and later she and Paul Mescal. However, these four relationships were never confirmed.
So with Jolie’s dating history, we’re only talking about the confirmed, A-list relationships in her life, from her forgotten first marriage to former co-star Johnny Lee Miller to her 12-year romance with Pitt. (And don’t forget her relationship with Jenny Shimizu!)
Check out Jolie’s entire confirmed dating history below:
Jolie’s first husband was an actor named Jonny Lee Miller, who she met on the set of the 1995 film Hackers. A year after meeting, they tied the knot in 1996, when Jolie famously rubber pants and a white T-shirt with Jonny’s name written on it in her blood for their wedding.
Their romance fizzled rather quickly, almost just as quickly as it started. Jolie even once said to The New York Times that their romance was such a whirlwind, saying, “You’re suddenly somebody’s wife. And you’re like, ‘Oh, I’m half of a couple now. I’ve lost me.’”
They finalized their divorce in 1999, but remained good friends.
Jenny Shimizu was Jolie’s first public relationship with a woman, and Jolie was truly so in love with her. The pair met while filming Foxfire, and the timeline is a bit hazy. From what we gather, the two had an on-again-off-again relationship from 1996 to 2000. In an archived 1997 interview per Cosmo, Jolie revealed her feelings for Shimizu, saying, “I probably would have married Jenny Shimizu if I hadn’t married my husband.” She continued, “I fell in love with her the first second I saw her.”
It’s unclear why they split up, but we do know that Shimizu reportedly invited her to her wedding to Michelle Harper, per The List.
Another brief fling Jolie had that’s been more or less confirmed was with Val Kilmer, who detailed about it in his memoir I’m Your Huckleberry. “I was rescued from an icy inferno of solitude by another angel,” he said. “Perhaps the most soulful and serious of them all. Angelina. When people ask me what Angelina is like, I always say she’s like other women and other superstars, but just more. More gorgeous. More wise. More tragic. More magic. More grounded. Is it worth it? Worth knowing people who require weeks of effort to understand even a little? Yes.”
Jolie and Billy Bob Thornton met on the set of Pushing Tin in 1999, and sparks flew immediately despite their 20-year age difference. Along with that, Thornton was with actress Laura Dern at the time, but suddenly dumped her to elope with Jolie in Vegas in 2000.
In fact, Dern told Talk magazine in 2000, per the List, “I left our home to work on a movie, and while I was away, my boyfriend got married, and I’ve never heard from him again. It’s like a sudden death. For one has there been any closure or clarity.”
They were one of the most controversial couples at the time, and the blood vial necklaces didn’t exactly help.
The pair ended up splitting up in 2003 for good, simply because they ended up going in different life paths and grew apart.
Jolie met her third husband Brad Pitt while they were filming the 2005 hit film Mr. And Mrs. Smith. When they met, Pitt was still married to Jennifer Aniston. Despite this, the two went public with their relationship soon after meeting on the set. They were together for years before marrying in Aug 2014 and shared six children together named Maddox, 21, Pax, 19, Zahara, 18, Shiloh, 16, and twins Knox and Vivienne, 14.
However, the pair ended up splitting up in late 2016 and while their divorce was finalized in 2019, they’re still going through quite a few messy disagreements including a lengthy custody battle and lawsuits.
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