Angelina Jolie has been at the center of Hollywood since the ’90s. She is not only an exceptional actress and model but also a humanitarian writer and director. Apart from her budding career, Angelina has also had a pretty active dating life.
Brad Pitt and Angelina Jolie were the ultimate head-turning couple. Unfortunately, the two have now divorced. Before the 12-year-long relationship with her ex-husband, Jolie had dated and married other men. Here’s a detailed dive into the ‘Mr. & Mrs. Smith’ actress’ dating history.
Related: Did Angelina Jolie And Billy Bob Thornton Wear Necklaces With Each Other’s Blood In Them?
Angelina Jolie’s Teenage Sweetheart
The actress had a boyfriend before stepping into the Hollywood industry. At the age of 14, the two young love birds were “like a married couple,” at Jolie’s house. She told Cosmopolitan in 2003, “When I was 14, I was either going to be reckless on the streets with my boyfriend or he was going to be with me in my bedroom with my mom in the next room because I was going to have a boyfriend. She made the choice, and because of it, I continued to go to school every morning and explored my first relationship in a safe way. So, in some strange way, she really did the right thing. It kept me out of trouble.” However, in 2016, she broke up with him to focus on her goals and ambitions.
Jonny Lee Miller
On the set of ‘Hackers’, Jolie found love in her co-star, Jonny Lee Miller. This was in 1994. However, when the production of the crime flick wrapped up, the two also ended their affair. However, they reconnected again in 1996 and got married. The Miller-Jolie couple couldn’t work for long, and a divorce was filed three years later.
Angelina Jolie Comes Out As Bisexual
After her brief affair with Jonny Lee Miller was over, Jolie started dating her ‘Foxfire’ co-star Jenny Shimizu. This was also the time that the ‘Salt’ actress came out as bisexual. Speaking with Rolling Stone in 2001, she said, “It had never crossed my mind that I was going to one day experiment with or kiss a woman, it was never something I was looking for. I just happened to fall for a girl.”
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Billy Bob Thornton
In 2000, Jolie married again. This time, to a man 20 years older than her. The Jolie-Billy Bob Thornton couple made several headlines as the two never shied away from PDA on the red carpet. Billy was smitten by the actress, and even though he was engaged to Laura Dern at that time, he still started dating Jolie. They had the most bizarre wedding ever, where the two said their vows in casual fits. They even had a vial hanging around their necks which had each other’s blood. Jolie even got a bold tattoo of Billy’s name ‘Billy Bob’, officiating her love for her husband.
In 2002, the two abruptly split and finally divorced the following year. Speaking with Vogue in 2004, Jolie remarked, “It took me by surprise too because overnight, we totally changed. Because we’re actors, we go away for months at a time and you grow and change separately. I think one day we had just nothing in common. And it’s scary but … I think it can happen when you get involved and you don’t know yourself yet. It’s taken me a while to grow up, and I still think I’m not even close to it yet. So I’ve kind of had to check myself: Don’t even consider a relationship for another seven, eight years.”
Brad Pitt
After promising herself that she wouldn’t “consider a relationship for another seven, eight years,” the actress was already in a relationship with Brad Pitt the next year. On the set of ‘Mr.& Mrs. Smith’, the co-stars had a romantic kindling with each other, and soon it became a controversy since Brad Pitt was married to Jennifer Aniston then. The couple was outed by Us Weekly when they posted a picture of Pitt and Jolie on Diani Beach in Kenya with Maddox, Jolie’s then three-year-old adopted son. They kept going strong, as the couple adopted two more children – Zahara from Ethiopia in 2005 and Pax from Vietnam in 2007. They also welcomed three biological children – Shiloh in 2006 and twins Knox and Vivienne in 2008. After dating for almost ten years, they quietly tied the knot in 2014. However, in 2018, Jolie filed for a divorce, her reason being, “I separated for the well-being of my family.” Currently, they are in the midst of a legal battle.
A Fling With The Weeknd
In July 2021, the 47-year-old actress was spotted with the ‘Blinding Lights’ singer at a series of dinners and concerts. The string of meets sparked romance rumors between the two. A source told Us, “Both Angie and Abel are telling people that they are just friends, but those who know them think something romantic is going on.” The source also added that The Weeknd “is in awe of” the Oscar winner. Jolie, however, has chosen to remain silent about the nature of her relationship with the musician.
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