Laura Dern was caught off guard when she discovered that her fiancé secretly tied the knot with Angelina Jolie behind her back. The unexpected marriage between Billy Bob Thornton and Angelina Jolie in 1999 shocked many due to their significant age gap and the fact that they were both in other relationships at the time.

Laura Dern, who was engaged to Billy Bob, learned about his marriage to Angelina at the same time as the public did, throwing her relationship plans into disarray. Their relationship began 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 led to a spontaneous wedding in Las Vegas in May 2000, leaving Laura blindsided. Laura described the situation, saying, “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.” This sudden turn of events left her feeling lost and confused, without any closure.

While Billy Bob expressed regret in a 2001 interview, he never explicitly acknowledged any wrongdoing, stating, “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 to the complexity of the situation, Laura and Angelina had a prior connection, with Laura having babysat Angelina when they were children. Bruce Dern, Laura’s father, recalled this time, mentioning, “Jon Voight’s a friend of mine, so I remember Laura babysat one night for Angelina when Angelina was 2 and Laura about 8.”

After the breakup, Laura received support from her friend Melissa Etheridge, who recounted helping Laura move out of her shared home with Billy Bob. Melissa shared, “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.”

In the aftermath, Laura moved forward with her life, eventually marrying Ben Harper and having two children. Billy Bob and Angelina divorced in 2002, prompting Billy Bob to step away from dating celebrities due to privacy concerns. He later married a puppeteer in 2014, seeking a quieter life away from the spotlight.

The situation involving Laura Dern, Billy Bob Thornton, and Angelina Jolie remains a topic of interest, raising questions about relationships, betrayal, and moving on.