The 41-year-old actor once said "I prefer ordinary girls - you know, college students, waitresses, that sort of thing," but his dating history would suggest otherwise.Here's a list of ladies who Leo has allegedly dated.In 2011, Di Caprio, then 36, dated 23- to 24-year-old Blake Lively.In 2012, he dated 22- to 23-year old Erin Heatherton.
November 2009: Leo and Bar enjoy a "secret" romantic getaway in the Bahamas. Since they've broken up something like three times in the last five years, you never know: Will they fight? Here, a time line of the glam pair's ups and downs: November 2005: Leo and Bar start dating when she's 20 (and he's 30). Before Bar, the actor dated supermodel Gisele Bundchen, who is now married to Tom Brady and has a child with him. September 2008: They are rumored to take some time off but reconciled months later. So while we're basking in that rumor's wonderful glow, let's try to make sense of their relationship.rich and famous older men—date much younger women all the time.It’s one of those accepted, ubiquitous social cues that tell women they get less fuckable as they age, but men don’t.It is reported that the relationship ended because she was interested in settling down, but Leo wasn’t ready to give up his playboy lifestyle.