Popsugar Celebrity Celebrity Couples Celebrities Who Broke Up and Got Back Together Breakup to Makeup: 38 On-Again, Off-Again Celebrity Couples July 11, 2018 by Monica Sisavat Solís View On One Page Photo 26 of 38 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 26 Kristin Cavallari and Jay Cutler 2010: Kristin started dating Jay. 2011: In April, the NFL quarterback popped the question in Mexico, but three months later, the couple called off their engagement. Their split didn't last very long, as the wedding was back on in November. 2012: The pair welcomed their first child, a son named Camden Jack Cutler. 2013: In June, Kristin and Jay tied the knot in Nashville. 2014: Kristin gave birth to her second child, Jaxon Wyatt Cutler, in May. 2015: The former The Hills star welcomed a baby girl named Saylor James Cutler in November. Related: A Sweet Look at Kristin Cavallari and Jay Cutler's Romance Previous Next Start Slideshow Celebrity CouplesCelebrity FactsCelebrity Breakups