Before Brad: Angelina Jolie's Bold Romance and Hollywood’s Most Controversial Love Triangle
Before her relationships with men became tabloid fodder, Jolie was open about her bisexuality. She had a well-known relationship with actress and model Jenny Shimizu, whom she met while filming Foxfire in 1996. Jolie once stated that she probably would have married Shimizu if she hadn’t met her first husband. Her candidness about her sexuality was considered controversial at the time.
Cine Chatter Team
Photo Credit: @ariasagay/X; @jennyshimizu/Instagram
When Brad Pitt famously divorced America’s sweetheart, Jennifer Aniston, to be with Angelina Jolie, it sent shockwaves through Hollywood. Pitt’s decision to leave Aniston for Jolie became one of the most talked-about celebrity breakups of all time. What made the situation even more captivating was Jolie’s past—a woman who had been openly bisexual, involved in a high-profile romance with actress and model Jenny Shimizu, before her relationship with Pitt took center stage.
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Long before she captured Brad Pitt’s heart, Jolie was candid about her attraction to both men and women. One of her most notable same-sex relationships was with Shimizu, whom she met on the set of Foxfire in 1996. Their connection was instant and intense, with Jolie later admitting, “I probably would have married Jenny if I hadn’t married my [first] husband.” At a time when such openness was rare in Hollywood, Jolie’s fearless acknowledgment of her sexuality made headlines.
Jolie’s past relationship with Shimizu, combined with her unapologetic honesty about her bisexuality, only added fuel to the fire when Pitt left Aniston to be with her.
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The media played up the narrative of Pitt divorcing the wholesome, beloved Aniston for the edgy, rebellious Jolie—who not only had a history of wild romances but had also been in a public relationship with a woman. This love triangle became the subject of endless fascination and speculation, with Jolie’s sexuality often used to paint her as the polar opposite of Aniston.
But Jolie never shied away from her past. She had always been open about her attraction to both genders, saying that love transcends gender. Her relationship with Shimizu wasn’t just a phase; it was a significant part of her life and identity. Jolie’s willingness to embrace her bisexuality challenged Hollywood norms and opened up conversations about sexual fluidity in an industry still dominated by heteronormative narratives.
As Jolie and Pitt’s relationship became more public, it didn’t erase her past or the fact that she had been one of the few stars at the time to openly discuss same-sex relationships. Even with the media frenzy surrounding Pitt’s divorce from Aniston, Jolie remained unapologetically true to herself, showing that love, in all its forms, is valid.
While her eventual marriage to Brad Pitt became a defining moment in her life, Angelina Jolie’s earlier romance with Jenny Shimizu was a bold statement of authenticity in an industry often hesitant to embrace fluid identities. Her bisexuality wasn’t just a headline—it was a part of who she was, long before Brad, and long after the tabloids moved on to the next story.
