In 1999, everyone was shocked when Billy Bob Thornton and Angelina Jolie got married unexpectedly. People were surprised because Billy Bob was much older than Angelina, and they were both already in relationships with other people.

One person caught off guard was actress Laura Dern, who was engaged to Billy Bob at the time. Laura found out about the wedding at the same time as everyone else, which messed up her plans for their relationship.

Billy Bob and Laura started dating in 1997, right after Laura broke up with Jeff Goldblum and Billy Bob was getting divorced from his fourth wife. They were engaged and getting ready to get married when Billy Bob met Angelina on a movie set in 1999.

Their fast-moving love story ended with a sudden wedding in Las Vegas in May 2000, which surprised Laura. She 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.” This left her feeling very sad and confused because she didn’t get any closure.

Although Billy Bob never admitted doing anything wrong, he did say sorry 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.”

To make things even stranger, Laura and Angelina knew each other before. Laura used to babysit Angelina when they were kids.

Laura Dern and ex-fiancé Billy Bob Thornton. Credit: Ron Galella, Ltd. / Ron Galella Collection / Getty.
Angelina Jolie and Billy Bob Thornton. Credit / Steve Granitz / WireImage / Getty.

Laura’s dad, Bruce Dern, remembered when Laura babysat Angelina Jolie when she was 2 and Laura was 8. This happened because Bruce and his friend Jon Voight were working on a movie together.

After Laura broke up with Billy Bob, her friend Melissa Etheridge helped her move out of their home. Melissa talked about how Angelina wasn’t treating Laura nicely when she was with Billy Bob. Melissa even had to break into their house to get Laura’s stuff out because things were so bad.

After all the drama, Laura moved on and married Ben Harper. They have two kids together. Billy Bob and Angelina got divorced in 2002. Billy Bob decided to stop dating famous people because he wanted more privacy. He got married again in 2014 to someone who works with puppets, trying to live a quieter life.

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