Kristin Cavallari and Jay Cutler
After hopping from Stephen Colletti to Brody Jenner to Nick Zano, former DWTS contestant Kristin Cavallari seemed to have finally found the love of her life in Chicago Bears quarterback Jay Cutler. The duo got engaged in April 2011, but went their separate ways when Jay called it off just three months later. After time apart, they rekindled their romance, announcing their re-engagement in November 2011. K-Cav gave birth to their baby boy Camden Jack on August 8, 2012, and she and Jay married in June 2013.