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.
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.
Amber Valletta
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.
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.
Gigi Hadid
It was about time that Leonardo DiCaprio started a thing with a Hadid sister. He had to at some point. It seems that right after breaking up with his longtime girlfriend Camila Morrone in August 2022, Leo started pursuing supermodel Gigi Hadid.
By September 2022, it was confirmed that Leo and Gigi were officially dating. Reportedly, Gigi and Leo keep it casual since Gigi doesn’t want anything serious after her breakup with her ex-husband and the father of her child, Zayn Malik.