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Angelina Jolie's Past Relationships

By Carol Cassada

Angelina Jolie is one of Hollywood's most popular stars. Not only is she an award-winning actress, but she's also an activist who works with numerous charities.

Despite her accomplishments in acting and humanity work, Jolie's personal life is often the focus of the media. The actress has had a string of high-profile relationships with other actors. She's been married and divorced three times. After her divorce from Brad Pitt, Jolie's personal life once again became tabloid fodder with gossip magazines wondering if she's dating again.

Recent rumors say that Jolie has entered the dating game again, but let's take a look back at some of her previous relationships.

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Jonny Lee Miller

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Angelina's first high-profile relationship was with actor Jonny Lee Miller. The two met on the set of the 1995 movie Hackers. Sparks flew between the two, and they married in March 1996 in a small, private ceremony. As both of their careers started to take off, the couple supported each other. Yet, their marriage would be short-lived. They separated a little over a year later, and their divorce became finalized in February 1999, and their split was amicable. Both Jolie and Miller have stated that they're still friends

Jenny Shimizu

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Angelina's sexuality has often been questioned by the tabloids. The actress was in an on-again, off-again relationship with model Jenny Shimizu for 10 years. Jolie's relationship with Shimizu leads to speculation about Jolie's preferences in a significant other. Jolie has talked about her sexuality and has stated she does consider herself bisexual. When Jolie was asked about her ex-girlfriend Shimizu, Angelina said it was love at first sight for her and Jenny. She even stated that odds were she would've married Jenny if she hadn't already met Jonny Lee Miller.

Billy Bob Thornton


Angelina Jolie and Billy Bob Thronton definitely sent tongues wagging with their relationship. The two met on the set of the 1999 film Pushing Tin, and in May 2000 married in a Las Vegas ceremony. The marriage stunned people, including Billy Bob's ex-fiancee Laura Dern, who was reportedly still in a relationship with Thornton at the time.

Angelina and Billy Bob's public displays of affection along with their strange ritual of wearing vials of each other's blood; made them one of Hollywood's most unique couples.

After three years together, the couple divorced in May 2003.

Brad Pitt

Angelina's most high-profile relationship came with her Mr. & Mr. Smith co-star Brad Pitt. The two were rumored to have had an affair on set, and that led to the demise of Pitt's marriage to actress Jennifer Aniston.

Shortly after his divorce from Aniston, Pitt and Angelina went public with their relationship. They quickly became Hollywood's hottest couple. Pitt became a father to Angelina's two adopted children Maddox and Zahara. In May 2006, their daughter Shiloh was born. The couple would also adopt another son named Pax, and in July 2008, Jolie gave birth to twins Knox and Vivienne.

After 8 years together, the couple finally tied the knot in August 2014. However, two years later Jolie filed for divorce. She and Pitt had a heated custody battle over their children but eventually reached an agreement. In April 2019, their divorce was finalized.

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