JONNY LEE MILLER: 1995 to 1999

angelina jolie dating history jonny lee miller
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Sorry, I can’t get over the fact that Angie’s first wedding outfit was rubber pants and a T-shirt with her husband’s name WRITTEN IN HER OWN BLOOD?!? She told The New York Times, “It’s your husband. You’re about to marry him. You can sacrifice a little to make it really special.” Anyway, she and Jonny Lee Miller met on the set of 1995’s Hackers and tied the knot in March 1996. They separated in 1999, but reportedly remained pretty good friends. Earlier this year, some people speculated that they were pulling a Bennifer when Angelina was seen leaving his apartment twice, but a source said it was actually just a playdate between their sons and that the two have been friends for years.

JENNY SHIMIZU: 1996 to 2000

angelina jolie dating history jenny shimzu
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Angelina met model and actress Jenny Shimizu while working on the 1996 film Foxfire, and tbh, it sounds like the sparks flew *instantly.* In 1997, Jolie told Girlfriends magazine, “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.” It seems like they dated on and off for a while before going their separate ways. There’s probably no lost love here — Jenny invited Angelina to her wedding in 2014, but she reportedly didn’t attend. We can’t say we blame her, tbh, going to an ex’s wedding sounds… super awkward?

TIMOTHY HUTTON: 1997

angelina jolie dating history timothy hutton
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Okay, this has never been *officially* confirmed, buuuuut Angelina and Timothy Hutton maybe kinda dated while filming the 1997 movie Playing God. If they did, it was all kept pretty low-key, possibly because Angelina was married to Miller at the time. But that’s none of my business.

BILLY BOB THORNTON: 1999 to 2003

angelina jolie dating history billy bob thornton
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These two were literally the definition of “doing the most.” Idk where to start. They met on the set of the 1999 movie Pushing Tin, and Billy Bob Thornton was a) almost 20 years older than Angelina and b) engaged to Laura Dern!!! But the heart wants what it wants, I guess, and Angelina and Billy Bob got married in 2000 in Vegas (Laura Dern said of the whole deal: “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.”)

Anyway, thus started a few years of Angelina and Billy Bob making everyone else kinda uncomfortable: they wore lockets with smears of each other’s blood around their necks, Billy told a red carpet interviewer that they had “f*cked in the car on the way here” while Angelina bit his face, they talked about installing a padded room in their house for “those moments in the middle of the night when you want to kill each other because you’re so in love.” (I…..don’t know). Then in 2002, they announced that they had adopted their son Maddox from Cambodia, though it later came out that Angelina had reportedly adopted him as a single parent. A few months later, they split and were officially divorced in 2003, but it sounds like they stayed relatively friendly. Angelina said in a 2008 interview, “I still love him dearly and think the world of him and I’m proud to have been his wife for a time. I don’t believe in regrets.” That’s a kinda shockingly sweet ending to a super weird relationship.

VAL KILMER: 2004

angelina jolie dating history val kilmer
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Angelina briefly dated Val Kilmer after they met filming 2004’s Alexander. Though their romance was short-lived, it sounds like it made an impact. He wrote in his memoir that she was “perhaps the most soulful and serious” partner he ever had and went on to say, “When people ask what she’s like, I say she’s like other women and other superstars, just MORE.” I can only hope my exes are out there writing similarly poetic things about me.

BRAD PITT: 2004 to 2016

angelina jolie dating history brad pitt
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Oh boy. Okay, so they met while filming Mr. & Mrs. Smith in 2004. There were definitely some rumors floating around about an on-set romance, but Brad was married to Jennifer Aniston at the time so it was all deny, deny, deny. Buuuuut in later interviews, they both admitted that they had fallen in love while working on this movie. In January 2005, Brad and Jen announce that they’re splitting up, and just a few months later, Brangelina is featured in a W Magazine photo spread titled ‘Domestic Bliss’, which basically confirmed it all. From there, it was off to the races: he legally adopted her children, they had a baby, made their official red-carpet debut—the whole works. Then, they welcomed twins in 2008, and later got engaged in 2012 (the ring cost 1! Million! Dollars!). They wed in 2014, and all seemed good… for like a minute. In 2016, news broke that Jolie had filed for divorce and the entire internet/world lost their minds. Her attorney released a statement saying Angelina made the decision “for the health of the family.”

MYSTERY REAL ESTATE MAN(?): MARCH 2018

A source told Entertainment Tonight in 2018 that Angelina was slowly moving on. The source claimed she had been seeing a “handsome, older-looking man who is a real estate agent.” Gotta love a good mystery man. But take this with a grain of salt: another source told People the same month that Ang “is absolutely not seeing anyone and will not be.”

THE WEEKND(?): JUNE 2021 TO…NOW, MAYBE?

angelina jolie dating the weeknd
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After Angelina and The Weeknd were spotted leaving the same Italian restaurant in June 2021, everyone was like, “are they dating????” And tbh, I’m still kinda wondering. They were also at the same private concert in July, and THEN, they had another cozy dinner in September at the same restaurant. Seems pretty date-y to me!

Then in an October 2021 interview, Angelina totally side-stepped a question about The Weeknd! The interviewer asked, “I have to know, because your kids are at the age where they have opinions. So, I have to know. Were they more excited that you were in The Eternals, or that you are friends with The Weeknd?” She replied, “They’re very excited about this film, if that’s what you’re asking.” She then took a moment and repeated, “They’re very excited about this film.” WHAT DOES IT MEAN?

But maybe we should all chill out a little bit because a source told E! News that there’s nothing romantic happening between them. “They are not dating. They have mutual interests and are enjoying putting their ideas together to see what they can come up with. They have been recently talking about partnering on a few humanitarian projects together. He loves talking about movies and the art form.”

I mean, I guess that’s still cool. Only time will tell!