Okay, honestly, I don't know when Angelina Jolie has time to sleep. Along with being one of the biggest A-list actresses since the '90s, she directs, she's written books, she's done tons of humanitarian work, and she's raising six kids. And we haven't even gotten to her dating life yet. In case you've been living under a rock, Angie just settled her divorce from Brad Pitt eight years after filing. But before there was Brad, Angelina Jolie's dating history was a ~journey~ in itself. There were PDA-filled interviews (could write a whole thesis on the red carpet energy of Angelina and Billy Bob Thornton) and blood sacrifices, and that's only the beginning. As for her post-Brad dating life? We've got some (possible?!) details on that too.
JONNY LEE MILLER: 1995 to 1999
Fun fact: Angie's first wedding outfit was rubber pants and a T-shirt with her husband's name WRITTEN IN HER OWN BLOOD?!? As she put it to 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 close. Back in 2021, 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—as the two have been friends for years.
JENNY SHIMIZU: 1996 to 2000
Angelina met model/actor Jenny Shimizu while working on the 1996 film Foxfire, and 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, and Jenny even invited Angelina to her wedding in 2014 (though she reportedly didn't attend).
TIMOTHY HUTTON: 1997
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
These two were literally the definition of "doing the most." 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, and the pair 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, and 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, the couple announced 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. 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."
VAL KILMER: 2004
Angelina briefly dated Val Kilmer after they met filming 2004's Alexander. Though their romance was short-lived, it made an impact. Val 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."
BRAD PITT: 2004 to 2016
Oh boy. So these two 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 announced that they're splitting up, and just a few months later, Brangelina was featured in a W Magazine photo spread titled 'Domestic Bliss', which basically confirmed it all.
From there, it was off to the races: Brad legally adopted her children, they had a baby, made their official red-carpet debut—the whole works. The pair welcomed twins in 2008, got engaged in 2012, and wed in 2014. Buuut then in 2016, news broke that Jolie had filed for divorce. Her attorney released a statement saying Angelina made the decision “for the health of the family.” It was a dramatic and lengthy settlement process to say the least, but eight years later they're officially over.
MYSTERY REAL ESTATE MAN: MARCH 2018
A source told Entertainment Tonight in 2018 that Angelina was slowly moving on. The insider claimed she had been seeing a "handsome, older-looking man who is a real estate agent." 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 (JUST A RUMOR)
After Angelina and The Weeknd were spotted leaving the same Italian restaurant in June 2021, everyone was like, "are they dating????" They were also at the same private concert in July, and THEN, they had another cozy dinner in September at the same restaurant.
Cut to an October 2021 interview, and 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.”
Meanwhile, 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."
AKALA: NOVEMBER 2024 (JUST A RUMOR!)
Angie and Akala were linked back in November, when a Daily Mail source spotted them emerging from a hotel in Venice. However, People shut this down with "She and Akala are not dating. She is friends with him and his partner, Chanelle, who was also there."
In other words, Angelina is currently single as far as the internet knows! But we'll update you if that should change.
