Ashlee Simpson & Pete Wentz

When they met at the MTV Video Music Awards in 2006, Pete Wentz knew he wanted to marry Ashlee Simpson, and after 2 years of dating, they finally tied the knot. In May of 2008, Ashlee and Pete were ready to start a life together. She even went out and gave birth to their son, Bronx Mowgli Wentz, that same year.

However, the Fall Out Boy rockstar and his wife eventually had a literal fallout. After all, things were moving pretty fast in their relationship and it left them overwhelmed, eventually deciding it was best to go their separate ways in February 2011. Their romance might have been short-lived, but they are on better terms these days. They even share custody of their wonderful 12-year-old boy. In fact, Bronx can go to any university of his choice without thinking about student loans, after all his parents have a great financial standing.