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It’s easy to look at Angelina Jolie now—the humanitarian work, the swarm of kids, the high-profile legal battles with Brad Pitt—and forget that she was once the ultimate Hollywood wildcard. Long before the "Brangelina" era redefined celebrity culture, there was a version of Angelina that existed in the hazy, grunge-fueled mid-90s. And at the center of that world was Jenny Shimizu.
If you weren't following the indie film scene or high fashion in 1996, it’s hard to explain how electric their connection felt. This wasn't some manufactured PR stunt. It was messy, intense, and, honestly, kinda revolutionary for the time.
The Foxfire Connection: How It Actually Started
They met on the set of Foxfire. If you haven't seen it, it's basically a cult classic about a girl gang. Angelina played "Legs" Sadovsky, a drifter with a buzzed head and a serious "don't mess with me" vibe. Jenny played Goldie, the gritty, cigarette-smoking rebel.
The chemistry wasn't just on camera. It was instant.
Angelina has been incredibly open about this—she's literally on the record saying she fell in love with Jenny the second she saw her. In a 1997 interview with Girlfriends magazine, she dropped a quote that still circulates today: "I probably would have married Jenny Shimizu if I hadn't married my husband." At the time, she was newly wed to Jonny Lee Miller.
Think about that for a second.
In the 90s, when most stars were terrified of being "outed," Angelina was just... being herself. She wasn't labeling it or making a political statement. She was just a 20-year-old woman who found someone who matched her intensity.
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Why Their Relationship Still Matters
People like to dismiss this as a "phase" or a wild youth thing, but that feels lazy.
The relationship between Jenny Shimizu and Angelina Jolie was significant because it broke the mold of the "Hollywood Starlet." Jenny wasn't a conventional "pretty girl" by 90s standards; she was a boundary-breaking Japanese-American supermodel with tattoos and an androgynous look that scared the traditional fashion world. She was the face of CK One, the fragrance that basically defined a generation.
When they were together, they represented a specific kind of freedom.
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The Reality of the "Long-Term" Rumors
There's a lot of misinformation about how long they actually dated. Some tabloids claim they were a thing for ten years. That’s probably a stretch.
The reality? They were intensely involved around 1996, but the connection lingered. Jenny has mentioned in later documentaries that for a long time, if Angelina called, she’d drop everything. Even when Angelina was with Billy Bob Thornton or starting her life with Brad Pitt, there was always this deep respect and a "what if" hanging in the air.
Honestly, they stayed friendly. When Jenny got married to Michelle Harper in 2014, she even invited Angelina. Angelina didn't go (she had just married Brad Pitt at the time, ironically), but the invite alone tells you there was no bad blood.
What We Get Wrong About This Duo
A lot of people think Jenny was just a footnote in Angelina’s dating history. That's a mistake.
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- Jenny wasn't a "fling." She was arguably Angelina's first major public experience with a woman that challenged her perspective on love and marriage.
- The timeline wasn't linear. Angelina was navigating her first marriage while dealing with these feelings. It was complicated.
- It wasn't just about rebellion. While the 90s "bad girl" image was a thing, their bond was based on being outsiders in an industry that wanted everyone to look and act the same.
The Takeaway for Today
Looking back at Jenny Shimizu and Angelina Jolie isn't just about celebrity gossip. It's about seeing the evolution of how we talk about bisexuality and fluid identities in the public eye. Angelina didn't wait for it to be "cool" or safe to talk about loving a woman. She just did it.
If you're looking to understand the real roots of the Angelina we see today—the woman who doesn't care about conforming to Hollywood's rules—you have to look back at 1996. You have to look at Foxfire.
Next Steps for the Curious:
If you want to see the spark for yourself, go find a copy of Foxfire. Don't just watch the clips on YouTube; watch the whole movie. It’s a time capsule of a specific moment in Portland, Oregon, and a rare glimpse at two people who were genuinely, unapologetically themselves before the world tried to polish them up. You might also want to look into Jenny Shimizu’s autobiography or her work with Calvin Klein to see how she paved the way for the queer-coded fashion we see on runways now.