After dating for over a year (starting in May 2013), Leo and 23-year-old Victoria's Secret model Toni Garrn broke up in 2014.
Tabloids claimed Leo being seen leaving a Miami nightclub with 20 women contributed to the split. But Kelly and Leo didn't last: by the beginning of 2016, they had broken up.
Although a source told The New York Daily News that Kristen was "the love of his life," she dumped him because of his immaturity and "posse of young model-hounds."The daughter of singer John Phillips, Bijou dated Leo in 1998.
They were spotted out together a few times during the height of the romance rumors, but nothing ever materialized. I don't know where the time is to date these days." He did admit the country star's "lovely" before the interview was over.
In February 2010, the country crooner was reportedly wooed by an older man: John Mayer.
Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005.
"We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best," she told Access Hollywood in 2009.