While plenty of people pine for the love that Leo had with BFF Kate Winslet in Titanic (and sort of wish that they would get together IRL), the 42-year-old isn't really doing anything wrong with sowing his oats — just look at his fellow former Hollywood bachelor George Clooney, who definitely landed a catch when he married wife Amal in 2014.Leo himself revealed in an interview last year that marriage "will come when that time comes," adding, "You can't plan it.
Over the years, the Oscar winner has romanced Hollywood actresses, Sports Illustrated swimsuit cover girls, and Victoria's Secret catwalk queens, all while trying to prove that he's just a regular guy who loves riding bikes around the city, texting his famous friends with club recommendations, and hitting the vape every once in a while.
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.
Admit it – you’re intrigued by Leonardo Di Caprio’s dating history. We have said they were probably a thing UNTIL it was reported he'd been seeing 19-year-old Dutch Victoria's Secret Pink model, Chelsey Weimar. See Leo’s dating history - from 1994 (when he was 20) to now…
As Sidebar of Shame as it is, it is kind of addictive to think about, and the more secret he gets with his gfs (as the briefer the dalliances) the more interesting it is.
Di Caprio seems particularly committed to the 20-25 age range, though; maybe it’s a very specific trophy-girlfriend archetype he’s looking for, or maybe he’s scared to date someone as grown and wise to the world as he is. He could also be nostalgic for that time in his own life, which was when he hit the big time in But there could be a more complex explanation for Di Caprio’s narrow sexual orientation.