In 1999, the unexpected union of Billy Bob Thornton and Angelina Jolie became a media sensation, leaving many in disbelief.

Not only did the couple navigate a substantial 20-year age difference, but they were also entangled with other partners at the time, adding an extra layer of intrigue.

Actress Laura Dern, Billy Bob’s fiancée, found herself among those blindsided. Laura revealed that she discovered her partner’s marriage to Angelina at the same time as the public, throwing an unexpected curveball into her relationship plans.

Billy Bob and Laura’s relationship commenced in 1997, shortly after Laura’s separation from Jeff Goldblum and Billy Bob’s ongoing divorce from his fourth wife, Pietra Dawn Cherniak, as reported by E! Online. Two years into their relationship, they were engaged and preparing for a wedding when Billy Bob crossed paths with Angelina on the set of Pushing Tin in 1999.

Their whirlwind romance led to a spontaneous wedding in Las Vegas in May 2000, catching Laura off guard. Reflecting on the abrupt turn of events, Laura shared (via InStyle): “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.” The situation left her with a sudden sense of loss and confusion, lacking closure.

While Billy Bob has never explicitly admitted wrongdoing, he expressed regret in a 2001 interview, stating (per the Mirror): “Others may say that you left our girl and married someone else. But it made me happy and somebody else happy. I’m sorry it caused pain.”

Laura’s father, Bruce Dern, recalled that time, saying, “Jon Voight’s a friend of mine, so I remember Laura babysat one night for Angelina when Angelina was 2 and Laura about 8 … because Jon and I were doing Coming Home.” Bruce added that Laura helped out when they stayed over at director Hal Ashby’s house.

Following the breakup, Laura received support from her friend Melissa Etheridge, who recounted assisting Laura in moving out of her shared home with Billy Bob.

In an interview with Andy Cohen on his SiriusFM radio show, Melissa shared (via the Sun): “I was around when Angelina was not doing nice things with Billy Bob to Laura Dern. I went through that on a personal level, and then to know the side of Jennifer and Brad. I helped Laura move out of her house with Billy Bob — I like broke into their home to get their stuff out because it was so nasty.”

After the fallout, everyone involved moved forward with their lives. Laura eventually married Ben Harper, with whom she shares two children, and has been linked to former NBA player Baron Davis.

Billy Bob and Angelina divorced in 2002, prompting Billy Bob to step back from dating celebrities due to privacy concerns. In 2014, he married a puppeteer, seeking a quieter life away from the spotlight.