It became a moment and a meme seen 'round the world.
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.
"It's so disappointing for people to hear that, because in the soap opera of the Kate and Leo story we fell in love at first sight and had a million snogs, but actually we never did. But we should never be saying that it's difficult because we are so bloody lucky. It's always a juggle, but isn't it for every working mother?
He always saw me as one of the boys; I've never really been a girly-girl. The thing for me personally that is a difficult transition is that my life at home is just so different to my life at work.
Leo and Gisele dated on and off between 19, and while their split was reportedly amicable, Gisele was the one who called it quits. We were very young, and we grew together in a lot of ways," she said in a 2009 Vanity Fair interview.
co-star Kate Winslet will always be the love of his professional life, not every single woman in the celebrity world loves and adores the newly-minted Oscar winner Leonardo Di Caprio. But there are plenty of women who are past loves and otherwise who've thrown more than a little shade Di Caprio's way after falling out of favor.