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Before Tom Brady, Gisele Bündchen dated Leo for five years, but ended it in 2005.
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 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's 1995 rumored fling with Naomi Campbell reportedly fizzled fast, but they became good friends.
More than 20 years later, they still get together to look hot on vacation, save Russian tigers, and photobomb 50 Cent.
Kristen Zang – Zang is a model that Di Caprio was reported to have dated on-and-off for 15 months from 1996 to 1997, when Di Caprio was really shooting into stardom, according to the NY Daily News. Emma Miller – Miller is a British model and socialite who had an on-and-off relationship with the star.