Back in 1998, Leo was browsing through a magazine one day and came across Amber’s gorgeous face. So, he called up his people and asked them to contact her agent, so they could meet. Soon, they went on a date and started a whirlwind fling that lasted a few months.
Amber Valetta started modeling at a young age, landing her first Vogue cover when she was barely 18 years old. She went on to grace American Vogue’s cover sixteen more times, not to mention her countless gigs as the face of Prada, Gucci, Versace, Armani, Chanel, Valentino, and Louis Vuitton.
Camila Morrone
Leo began dating Camila Morrone when the young Argentine model and actress was just 22 years old. When Morrone was asked what his thoughts were about her age gap with the iconic actor, she said: “I just think anyone should be able to date who they want to date.” Of course, this opinion stops making sense if the age gap was just a bit larger, as there's still an important weight to age in a relationship.
It appears that DiCaprio prefers to date beautiful models without caring too much about maturity, which might explain why he keeps hooking in young and impressionable models that are younger than he was more than two decades ago. The two are very public about dating each other and their mutual love, but the age difference is rather startling when you notice that she could easily pass as his daughter when you look at a picture of them holding hands.
Kate Winslet
One of the more known friendships in Hollywood is that of Leonardo DiCaprio and Kate Winslet. The eternal bachelor and the British actress both got a huge boost to their careers when they starred in James Cameron's Titanic as the eternally romantic and tragic couple of Jack Dawson and Rose DeWitt Bukater.
The two claim to be good friends and have excellent chemistry together, although they claim to have never dated each other. Winslet often talks in interviews about their friendship but claims that this is one of those rare cases where romance just never really developed. It seems that the two might just be the perfect couple for each other, as both of them are single, of the same age, and have almost parallel life experiences. We can only cross our fingers and hope to one day see a relationship between the two because it seems that this might just be the perfect one for the two beautiful stars.
Liv Tyler
Although this was a short fling, it's still worth mentioning because it had everybody wondering back in the 90s. It turns out that Leo DiCaprio and the stunningly beautiful Liv Tyler were supposed to co-star in a movie. Leo and Liv met at a party. Those party photos of the pair had everyone conjuring up wild theories, imagining what DiCaprio would think of becoming Steven Tyler’s son-in-law.
Ultimately, Liv Tyler went on to marry Royston Langdon, with whom she had a son, and then got together with David Gardner, with whom she has two children.
Virginie LeDoyen
It seems that DiCaprio was as smitten as we were with his French co-star in "The Beach." Even though the movie was not a commercial success by any means, it was worth it just to see the chemistry between actress Virginie LeDoyen and Leo on screen.
It seems that chemistry translated off the screen when the two were reportedly seen together on several occasions during the filming and after the movie wrapped up. The romance was brief, and LeDoyen went on to marry three times and have three lovely children.