Angelina Jolie Dating History: Brad Pitt, Billy Bob Thornton, and More!

The admirers of Angie! Because of her blossoming cinematic career in the ’90s, Angelina Jolie’s personal love life has become a hot topic. In the late 1980s, at the age of 14, the Academy Award-winning actress had her first sex partner. Jolie’s mother, Marcheline Bertrand, allowed him to live in their home, an odd arrangement that Jolie defended years later, even though she never officially revealed his identity.

‘The decisions my mother made for me were not irresponsible,‘ she told Cosmopolitan in 2003. ‘My mother is very compassionate and supportive. Having a boyfriend when you’re 14 means you’re either going to be irresponsible on the streets or you’re going to be in your room with him with your mom next to you.

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She made the decision, and as a result, I was able to attend school every day and begin my first relationship in a safe environment. So, in a twisted way, she was correct to do what she had to do. For me, it was a lifesaver.” After dating her high school boyfriend for two years, Jolie said they “lived like a married couple” to The Sun in 2011. Despite this, when she was 16, she broke up with him to concentrate on her acting career.

When the Los Angeles native finally found love again in 1994, it was a long time coming. She began a romance with her co-star, Jonny Lee Miller while filming Hackers in 1995. After the shoot was over, they didn’t keep in touch, and she started seeing her Foxfire co-star Jenny Shimizu.

It never occurred to Angelina Jolie that she would one day experiment with or even kiss a woman, and it wasn’t anything she was seeking for. “I just happened to fall in love with a woman.” It was through Miller that the Gia actress rekindled her romance with her ex-boyfriend Shimizu. They got married in 1996 but divorced after three years.

During the dying days of her and Miller’s marriage, she told Rolling Stone, “I wasn’t even a decent friend because I was simply missing.” When I was younger, I’d go on long drives or film a movie and stay in motels for months at a time, never seeing anyone or doing anything socially. “I couldn’t bring myself to relax and enjoy the simple pleasures of life.”

In the year 2000, Angelina Jolie stunned the world by getting married a second time, this time to actor Billy Bob Thornton. The couple’s union, however, did not last long, as they abruptly parted ways in 2002 and went through with their divorce that year.

During an interview with Vogue in 2004, she revealed that she and her husband had “completely changed overnight.” As actors, we’re often absent for months at a time, and you’re left to your own devices.” I believe that at some point, we had nothing in common at all. And it’s frightening, because… In my opinion, it can happen when you get involved and don’t yet know who you are. In my opinion, I’m not even close to being a fully-fledged adult. To avoid a relationship for another seven or eight years, I’ve had to restrain myself: “Don’t even think about it!”

While filming Mr. & Mrs. Smith, Lara Croft, the Tomb Raider star, betrayed her pledge to herself by falling in love with Brad Pitt. At the time of the controversy, he was married to Jennifer Aniston, which shook Hollywood. A photo of Jolie and Pitt on Diani Beach, Kenya, with her 3-year-old son, Maddox, who she adopted from Cambodia, broke the news of their relationship in 2005.

It wasn’t long before Brangelina (as they came to be called) had three children of their own: Shiloh (born in 2006), Knox (born a year later), and Vivienne (in 2008). They exchanged vows in 2014 in front of a small gathering of family and friends, including their young children. They were divorced in 2019 after Jolie filed for it in 2018.

‘I split for the sake of my family,’ Maleficent’s star said in a Vogue interview in 2020. My decision was correct. In the meantime, I’m focusing on their healing.”

Jolie’s high-profile romances are detailed below!

Jonny Lee Miller

Jolie married Miller in 1996, over two years after filming Hackers together, in a civil ceremony attended only by Jolie’s mother and Miller’s best friend. White shirt with the blood-stained name of the groom on the back of the bride’s white rubber trousers. A clean surgical needle was used to draw the blood from her own arm, she later admitted to The New York Times. Because of their hectic schedules, the couple was unable to spend time together and eventually divorced in 1997.

Angelina Jolie and Jonny Lee Miller
Angelina Jolie and Jonny Lee Miller

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In 1999, she filed for divorce, and the proceedings were concluded in December of the same year. “Miller is still a terrific friend,” Jolie said to BuzzFeed in 2014.

Jenny Shimizu

Jolie was smitten with her Foxfire co-star, whom she dated before marrying Miller. “If I hadn’t married my husband, I probably would have married Jenny Shimizu. In 1997, she told Girlfriends magazine, “I fell in love with her the first time I saw her.”

Angelina Jolie and Jenny Shimizu
Angelina Jolie and Jenny Shimizu

Billy Bob Thornton

Pushing Tin, a 1999 comedy-drama in which Jolie and Thornton starred as a married couple, is where Jolie first met Thornton. During a trip to Las Vegas in 2000, they discreetly tied the knot. At the time, the actor and Laura Dern were still engaged. Talk magazine quoted Dern later that year as saying that “My lover married while I was overseas, and I’ve never heard from him again.” During an interview with Entertainment Weekly in 2008, Jolie described the necklaces she and Thornton wore in 2001 as “a beautiful gesture.”

Angelina Jolie and Billy Bob Thornton
Angelina Jolie and Billy Bob Thornton

As soon as they declared their plan to adopt Maddox jointly in 2002, Jolie proceeded on her own, months later. In 2003, they were able to finalize their divorce. “Good friends” is how Thornton described his relationship with Jolie in an interview with Us in 2019.

Brad Pitt

Pitt and Aniston’s divorce was blamed on Jolie’s on-set romance with Mr. & Mrs. Smith co-stars Angelina Jolie and Brad Pitt. The star of Girl, Interrupted, however, denied they had a physical affair, claiming on the Today show that year, “I wouldn’t be attracted to a man who would cheat on his wife.” That being said, the romance between the Brangelina’s picked up speed quite quickly. It was around the end of 2005 that she became pregnant with Shiloh.

Angelina Jolie and Brad Pitt
Angelina Jolie and Brad Pitt

Pitt adopted Pax in 2008, the same year that Jolie gave birth to Knox and Vivienne, making him the legal father of Maddox and Zahara. The By the Sea stars got engaged in 2012 and now have a brood of eight. Two years later, they married at their Château Miraval in France. In 2016, Jolie filed for divorce. The dispute over their children’s custody has delayed the finalization of their divorce.

The Weeknd

A series of dinner and concert meetings between the actress and the singer sparked relationship suspicions in July 2021. According to a source who spoke to Us exclusively in September 2021, “both Angie and Abel are telling people that they are simply friends, but others who know them think something romantic is going on.” On the other hand, Angelina Jolie has been tight-lipped about her relationship with the singer of “Blinding Lights.”

Angelina Jolie and Abel
Angelina Jolie and Abel

That doesn’t stop people from guessing about her relationship status since her split from Brad, even if there have been no public romances that she’s confirmed. A source close to The Weeknd has confirmed exclusively to HollywoodLife that the pair are merely pals. However, the relationship between him and Angie and her children is still in its infancy, as he has only been in contact with her for professional purposes and not as a romantic interest. Angelina is currently more preoccupied with her family, therefore it would be premature to declare them a couple, according to the sources.