First, there was Kristin's admission that she contemplated divorce "every day for two years" before the split and the revelation that the production crew behind her show, Very Cavallari, had captured the reality of their marriage in scenes they decided never to air for the sake of the pair's three children.
Most recently, the pair have both been linked with other people — but even this wasn't without its complications.
After Madison posted an Instagram Live where she mocked Kristin and made disparaging comments about her parenting skills, Kristin and Jay posted selfies with matching captions.
"The world is full of users. 10 years. Can't break that," they wrote alongside the selfie in apparent reference to Madison and the strength of their bond after a decade together.