2. Ashton Kutcher and Demi Moore
This pair surprised everyone not only when they began dating but also when they eventually got married in 2005. Their marriage lasted six years before Kutcher’s cheating led to its demise. During their time together he went on to star in the hit series Two and a Half Men while Moore’s super stardom from the 80s and 90s had faded. Without a signed prenup to fall back on, their settlement battle raged on for two years before they finalized it in 2013. Moore is worth $150 million but was still able to wrangle spousal support from Kutcher. The final amount hasn’t been made public but Kutcher ended up paying more than he expected to just to close this chapter and move on.
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