Angelina Jolie Dating History: From Her First Marriage To Brad Pitt To Now

Angelina Jolie's love life has long been of public interest! Find out more about her dating history from Jonny Lee Miller to Brad Pitt here!

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Angelina Jolie has been one of the most celebrated actresses for decades! The daughter of actors Jon Voigt and Marcheline Bertrand, Angelina, 47, began her career in entertainment as a kid, making her on-screen debut with her dad in 1982. Since then, she’s gone on to star in a wide array of hits, including Girl, Interrupted, which she won an Oscar for, and many more hits, like Maleficent, Changeling, and Eternals.

Other than her movies, Angelina’s personal life has long been a topic of discussion among her fans! From her charitable endeavors to her dating life, fans have followed the actress closely throughout her career. Throughout her career, she’s been married three times. Find out everything you need to know about Angelina’s dating history here!

Angelina’s first boyfriend

When the Maleficent star was 14, she had a boyfriend move in with her family, she revealed in a 2003 interview with Cosmopolitan. Angelina credited her mom with being “caring” in making the decision to let her boyfriend move in. “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,” she said, saying that by having him stay with her, she went to school every day still. “So in some strange way, she really did the right thing. It kept me out of trouble.”

Jonny Lee Miller

Angelina and Jonny dated after meeting on the set of ‘Hackers.’ (Shutterstock)

Angelina’s first high-profile relationship came during one of her early breakout roles in Hackers in 1995. Angelina started dating her co-star Jonny Lee Miller, 49. The pair kindled a romance after the production ended, and they got married in March 1996. Angelina opened up about the sudden marriage in an interview with The New York Times. “You’re suddenly somebody’s wife. And you’re like, ‘Oh, I’m half of a couple now. I’ve lost me.'”

The pair ended up splitting up after a year of marriage, and their divorce was finalized in 1999. Despite the divorce, the exes seem to be on good terms! The Hackers stars were spotted getting dinner together in Los Angeles in October 2021, and the actress even reportedly introduced her ex to her sons.

Jenny Shimizu

After her relationship with Jonny, Angelina had a brief romance with Jenny. (Shutterstock)

Angelina met model and actress Jenny Shimizu, 54, while the pair were working on the movie Foxfire. While the exact timeline of their relationship isn’t clear, they appeared to have an on-and-off romance from 1996 to 2000. The Salt actress gushed about Jenny in a 1997 interview with Girlfriends, per Cosmopolitan. “I probably would have married Jenny Shimizu if I hadn’t married my husband. I fell in love with her the first second I saw her,” she said at the time.

Angelina’s romance with Jenny was an eye-opening experience for her. “[I was] surprised when I suddenly found myself having these feelings I always had for men, but for a woman,” she said in a 20/20 interview, per Us Weekly. Like with Jonny, it seems the two are still friends despite their relationship not working out. Jenny reportedly invited Angelina to her 2012 wedding to Michelle Harper, per The List.  

Billy Bob Thornton

Billy Bob and Angelina walk the red carpet at the 2002 Golden Globes. (Shutterstock)

After her divorce from Jonny was finalized, Angelina married Billy Bob Thornton66, in 2000. The pair became instant media sensations mainly for their eccentric-seeming shows of affection, notably wearing a vial of each other’s blood around their necks. Despite it sounding strange, the Bad Santa star has said that it was much less gruesome than it sounds in a 2018 interview with the HFPA’s In Conversation podcast, saying that the actress came home with a “simple” kit. “‘Hey, let’s poke our finger with a pin and smear a little on there, and when we’re away from each other, we’ll wear the necklace.’ That was that easy, but by the time it came out in the press, it sounded like we were wearing a bucket of blood around our necks,” he said.

The pair also had some more typical shows of affection. Billy penned a song for her called “Angelina” for his 2001 album. The actress also got a tattoo with Billy’s name in it, but she’s since gotten it removed, according to The Sun. The couple ended up splitting up in 2002 and finalizing their divorce in 2003, but it appears that they’re both still on good terms with each other!

Brad Pitt

Angelina’s longest-running relationship was with Brad Pitt. (Shutterstock)

Angelina met her third husband Brad Pitt, 58, who would be her most highly-publicized relationship, while they were filming the 2005 film Mr. And Mrs. Smith. The couple ended up going public with their romance in 2006, and they were dubbed “Brangelina” throughout their 12-year-romance. The couple got married in August 2014. During their relationship, Brad also adopted Angelina’s three adopted children (Maddox, Pax, and Zahara), and the pair had three biological kids (Shiloh, Knox, and Vivienne) together.  Throughout their relationship, Brangelina were also media darlings, with many people following their relationship closely.

Unfortunately, the pair ended up separating in September 2016. After three years, the pair’s divorce was finalized in 2019, but the divorce turned messy after the fact. The couple engaged in a long, difficult custody battle over their children. Brad had also sued Angelina after she sold her stake in a winery, which they both co-owned.

Rumored Romance After Divorce

Since divorcing Brad, Angelina was seen spending a lot of time with The Weeknd, but they might be just friends! (Shutterstock)

Since the split from Brad, Angelina hasn’t had any public romances that she’s confirmed, but that hasn’t stopped people from speculating on her relationship status since the breakup! The Oscar winner was seen out to dinner with “Blinding Lights” singer The Weeknd in July 2021, and while fans have wondered whether they’re just friends or something more, a source close to the singer revealed to HollywoodLife exclusively that they’re just friends. “He has gained a great friendship with Angie and has met her kids, but it has been very much on the up and up when it comes to a full-on relationship as it has been friendly and business only. It would be very premature to say that they both are a couple as Angelina is more focused on her family right now,” they said.