In 1999, the world was taken by surprise when Billy Bob Thornton married Angelina Jolie out of the blue. The unconventional couple, with their significant age difference and existing relationships, shocked everyone around them.

Among those caught off guard was actress Laura Dern, who was engaged to Billy Bob at the time. Laura learned about the wedding at the same time as the public, completely blindsided and devastated. The news shattered her plans for their future together.

Laura and Billy Bob had begun dating in 1997, shortly after Laura’s breakup with Jeff Goldblum and Billy Bob’s divorce from his fourth wife. Their love grew, and they were even preparing for marriage when Billy Bob met Angelina on a movie set in 1999.

Their whirlwind romance concluded with a spontaneous wedding in Las Vegas in May 2000, leaving Laura feeling incredibly sad and confused. As she recalls, “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 lack of closure added to her heartache.

Although Billy Bob never officially acknowledged any wrongdoing, he did express remorse in a 2001 interview, saying, “Some 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.” While his apology didn’t erase the hurt, it provided a small sense of acknowledgement.

To make the situation even more peculiar, Laura and Angelina knew each other from childhood. In fact, Laura used to babysit Angelina when they were young. Laura’s father, Bruce Dern, recalls how Laura, at the age of 8, looked after a 2-year-old Angelina during a movie project involving Bruce and his friend Jon Voight.

After parting ways with Billy Bob, Laura found support in her friend Melissa Etheridge, who helped her move out of their shared home. Melissa spoke of how Angelina had not treated Laura with kindness during their time together. Things got so bad that Melissa had to break into the house to retrieve Laura’s belongings.

Eventually, Laura found solace and happiness with her husband, Ben Harper, with whom she shares two children. As for Billy Bob and Angelina, their marriage ended in divorce in 2002. Billy Bob, desiring a more private life, chose to avoid dating famous individuals and ultimately remarried in 2014 to someone involved in puppetry.

The story of Laura Dern’s unexpected heartbreak is a reminder that even in the world of Hollywood, relationships can be unpredictable and painful.