Who Has Leonardo DiCaprio Dated?

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It goes without saying that Leonardo DiCaprio is a hit with the ladies — especially ladies who are probably tall, are probably blond, and have probably walked a runway. 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.

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 41-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. It’s just going to happen when it happens.” For now, we’re looking back on Leo’s relationship history, from the true romances to the rumored flings. Keep reading to see them all now.