You wouldn’t know it based on his dating history, but Leonardo DiCaprio isn’t young anymore. The Oscar winner turned 50 on November 11, making him a far cry from the fresh-faced young hunk the world fell in love with in Titanic. But perhaps Leonardo DiCaprio still feels young, and that’s why he famously only dates women aged 25 and under.
When DiCaprio was 25, it was 1999 and he was acting in The Beach, playing a young American backpacker who finds a deserted island paradise in Thailand (which turns out not to be quite such a paradise in the end). But DiCaprio’s career began much earlier, when he starred in Growing Pains as a teenager. He was only 22 when he played Romeo in Baz Luhrmann’s Romeo + Juliet, and when he froze to death in the Atlantic Ocean in Titanic in 1997, he was just 23 years old.
Back then Leo was known for his floppy blond hair and boyish smile—which we have to admit is a far cry from the middle-aged man we know and love today. So if you feel like going back in time to an era when Leonardo DiCaprio was the same age as his current girlfriends, here you go.
