Who is Leonardo DiCaprio dating? Who Leonardo DiCaprio dated; list of Leonardo DiCaprio loves, ex girlfriends; breakup rumors. The loves and relationships of Leonardo DiCaprio, listed by most recent. From Bar Refaeli up are rumored hookups and one-night stands. Looks like Leo has really gotten around! It's actually kind of funny to see that the Leonardo DiCaprio movies list has less items than his hookups list. But, if you were Leonardo wouldn't you take advantage of your fame and good looks too?