12. Bar Rafaeli
Leo and Bar Rafaeli had an on-and-off relationship for a handful of years during the early 2000s. This is one of his more “serious” past relationship, a relationship that had many people buzzing about whether Bar was the woman who would finally get Leo to settle down. Bar Rafaeli is one of the world’s most indemand models having been voted number 1 in Maxim magazine’s Hot 100 List of 2013.
The Israeli-born beauty has modeled for a wide variety of brands, including Chanel, Gap and True Religion, among others. Bar was also the cover girl for 2009’s Sports Illustrated edition. In addition to her modeling work, Bar also hosts the Israeli edition of The X-Factor.