In 1999, the unexpected marriage of Billy Bob Thornton and Angelina Jolie shocked everyone. They not only had a big 20-year age gap but were also involved with other partners, making their union even more surprising.

One person who was particularly stunned was actress Laura Dern, Billy Bob’s fiancée at the time. Laura discovered her partner’s wedding to Angelina at the same time as the general public, which was a huge shock.

Billy Bob and Laura started dating in 1997, soon after Laura’s breakup with Jeff Goldblum and while Billy Bob was divorcing his fourth wife, Pietra Dawn Cherniak. After two years together, they were engaged and planning their wedding when Billy Bob met Angelina on the set of “Pushing Tin” in 1999.

Their fast-paced romance led to a sudden wedding in Las Vegas in May 2000, leaving Laura completely blindsided. Reflecting on the situation, Laura said, “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.” She felt a sudden loss and confusion, with no closure.

Billy Bob never outright admitted any wrongdoing, but he did express some 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 to the oddity, Laura and Angelina had a prior connection. Laura had babysat Angelina when they were kids.

Their fathers, Bruce Dern and Jon Voight, were friends. Laura recalled babysitting Angelina when she was two years old and Laura was eight, making the situation even more unexpected.

After the breakup, Laura found support from her friend Melissa Etheridge, who even helped her 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. 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.”

Eventually, everyone moved on with their lives. Laura later married Ben Harper and has been linked to former NBA player Baron Davis. Billy Bob divorced Angelina in 2002 and chose to avoid dating celebrities for privacy reasons.

He found happiness with a puppeteer, whom he married in 2014, seeking a quieter life away from the spotlight.

What do you think of this surprising situation? Let us know in the comments!