Sep 13, · A-list actor Leonardo DiCaprio is one of Hollywood's most eligible bachelors and he has an undeniable weakness for the industry's hottest models! Check out which lovely ladies Leo has been linked to over the years . DiCaprio was twelve when he and Tobey Maguire became best friends. After meeting him through auditions, DiCaprio was drawn to Maguire because of their shared experiences—both were raised in Los Angeles by single mothers. “When I want someone to be my friend, I just make them my friend. See the latest Leonardo DiCaprio news on movies, Oscar award nominations, red carpet and girlfriend updates after the Titanic star's split from Nina Agdal.