Who: Oscar-winning actress, producer, director, and humanitarian Angelina Jolie, 46; and model and actress Jenny Shimizu, 54.
How They Met: Jolie first noticed Shimizu when they were initially cast in the 1996 film Foxfire.
At first, Jolie said she feared Shimizu was going to steal her role, but she was preoccupied … "I fell in love with her the first second I saw her," Jolie reportedly told Girlfriends magazine in 1997.
According to Rhona Mercer's biography, Angelina Jolie: Portrait of a Superstar, Shimizu said that she and Jolie would visit strip clubs together and there "was tension" between them. "The second week of filming, we kissed," she reportedly said.
Despite the instant attraction, Jolie was also involved with her husband-to-be, Jonny Lee Miller.
"He was around when I was figuring things out about myself, when I was realizing that I was attracted to women also," Jolie told the magazine. "When I realized that somebody like Jenny could be a deep love for me, he realized it, and he took it very seriously. If anything, he didn't treat it just like some sexy thing."
In fact, Jolie went as far as to say that she "probably would have married" Shimizu if she hadn't wed Miller.
Shimizu reportedly said that Jolie took her and Miller out to dinner one night to tell them how she felt. "She was honest — that's how she's been her whole life," Shimizu remembered.
Why We Loved Them: Meeting Shimizu began an important period of self-discovery for Jolie.
"I realized that I was looking at [Shimizu] in a way that I had looked at men," the Girl, Interrupted star reportedly told Rolling Stone. "And it was great, and it was a discovery. 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."
Years later, in 2003, Jolie described herself to Barbara Walters as "a very sexual person who loves who she loves, whatever sex they may be."
When They Peaked: Though little is known for certain about the relationship, it's clear that there was an abundance of support between the co-stars.
When asked to name her favorite actor to work with, Jolie referenced Shimizu. "She's great," she said of the model. "We had a lot of fun."
The Breakup: It's unclear when Jolie and Shimizu stopped seeing each other, but the U.N. Special Envoy carried on several serious relationships with famous men over the next two decades.
Where They Are Now: After splitting with Miller in the late '90s, Jolie went on to marry Billy Bob Thornton in 2000 (the fiery union came to an end in 2003). Then, Jolie got together with her Mr. & Mrs. Smith co-star Brad Pitt, who adopted her son Maddox (now 20). They welcomed five more children together — Pax, 17, Zahara, 16, Shiloh, 15, and twins Vivienne and Knox, 13 — before marrying in 2014. The couple announced their separation in the fall of 2016.
Jolie's latest project, Marvel's Eternals, opens in theaters Nov. 5.
Shimizu wed brand consultant Michelle Harper in 2014. She allegedly even invited Jolie to the wedding. "It's not like I wanted her to walk me down the aisle or anything, but it would have been a really cool thing if she'd come," Shimizu said of the invitation, according to Dish Nation.
#TBT: Check in every Thursday as we throw it back to some of our favorite celebrity couples of all time.
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