Jennifer Lopez & Chris Judd – $14 Million
After Jennifer Lopez called it off with Sean Combs, she began a relationship with Chris Judd, a former backup dancer. The two eventually got married, but the union lasted less than a year overall.
Ron Perelman & Ellen Barkin – $20 Million
Here’s a fun fact: Ron Perelman is the 36th richest man in America! It was in 1999 that he was introduced to actress Ellen Barkin at an Oscar after-party hosted by Vanity Fair. She became his fourth wife a year after. After five years together, they filed for divorce. Sources say that Ellen was able to receive a settlement of anywhere between $20 million and $65 million.