Chace Crawford's Dating History, From Carrie Underwood to Rebecca Rittenhouse

The couple started dating in May 2007 and broke up in April 2008, per Cosmopolitan. According to People, Crawford "flew to visit her [and] went on tour with her." Soon after, Underwood told Extra (per People) that he had broken things off via text, though she added that "we both knew it didn't work and [had] no hard feelings at all whatsoever." However, sources later told People that Underwood had ended things. Regardless, Underwood now shares two children with husband Mike Fisher.