In 1999, the unexpected union of Billy Bob Thornton and Angelina Jolie shocked the world. This unlikely couple not only had a significant 20-year age gap but were also involved with other partners at the time, adding to the intrigue.

Among those taken aback was actress Laura Dern, Billy Bob’s fiancée. Laura discovered her partner’s wedding to Angelina at the same time as the general public, throwing a curveball into their relationship plans.

Billy Bob and Laura began their relationship in 1997, shortly after Laura’s split from Jeff Goldblum and Billy Bob’s ongoing divorce from his fourth wife, Pietra Dawn Cherniak. After two years together, 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 culminated in a spontaneous wedding in Las Vegas in May 2000, catching Laura completely off guard. Reflecting on the abrupt turn of events, Laura shared, “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 feeling a sudden loss and confusion, with no closure in sight.

While Billy Bob has never explicitly admitted any wrongdoing, he did express regret in a 2001 interview, saying, “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.”

Adding an odd twist to the story, Laura and Angelina had a prior connection. Laura had babysat Angelina when they were children. Their fathers, Bruce Dern and Jon Voight, were friends, and Laura recalled babysitting Angelina when she was two years old and Laura herself was eight. This connection made the whole situation even more unexpected.

In the aftermath of the breakup, Laura found support from her friend Melissa Etheridge, who even helped her move out of her shared home with Billy Bob. Melissa revealed, “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.”

Everyone involved eventually moved forward with their lives. Laura later married Ben Harper and has since been linked to former NBA player Baron Davis. Billy Bob, on the other hand, divorced Angelina in 2002 and decided to steer clear of dating celebrities due to privacy concerns. He found happiness with a puppeteer, whom he married in 2014, seeking a quieter life away from the spotlight.