If there’s one woman who clearly needs no introduction in this list, it’s Paris Hilton. This social starlet and child to the Hilton family, who owns the famous hotel chains, is the only person on this list that became famous and super successful through family affiliation, way before any talent or skill was thrown into the mix. While she’s not exactly the regular type of girl that Leonardo DiCaprio usually goes for, the two were often seen together back in 2000, and rumors began to rise that they were involved in some way. Either way, this romance didn’t last long either because DiCaprio had already tasted the forbidden fruit of Victoria’s Secret models at that point, which meant that no rich socialite was going to saturate his appetite for models.
Paris Hilton is also one of the richest people on this list, with much of her income coming from her wealth of connections in the business and entertainment industries. She often gets paid tens of thousands of dollars (and even more) just to appear in various popular nightclub venues and events. She also likes to DJ in her free time and owns her very own fashion line.
Juliette Perkins
It seems that while Dicaprio is getting older, the girls he is dating keep getting younger. At this point, it looks like the only thing stopping the actor from dating 18, 17, and 16-year-old models are statutory limits. Leo was recently spotted enjoying a great time with teenage New Zealand model Juliette Perkins. The model was signed with IMG at age 15 and has been a prominent model there since. While models usually turn into Victoria's Secret models and then begin dating DiCaprio, this one decided to go the opposite way and started by dating the "Titanic" star. The two were also seen clubbing together in several venues, even though she's currently under the legal drinking age in the United States.
The young model has almost thousands of followers on Instagram and a YouTube channel with various vlogs and makeup tutorials.
Brittany Daniel
One of Leonardo DiCaprio's first films that helped set up the launching of his career was Scott Kalvert's biographical crime drama film "The Basketball Diaries." It tells the true story of a promising high school basketball player who turns into a heroin addict. Despite not making a lot of money at the box office, "The Basketball Diaries" was fairly well-reviewed.
Twin sisters and actresses Brittany Daniel and Cynthia Daniel played together in the film as Blinkie and Winkie, respectively, and that's how Brittanny met the young DiCaprio. The two were apparently involved and had a fling together. This makes sense, seeing how Brittanny perfectly fits the actors' regular lineup of women. Brittanny is best known for her role as Jessica Wakefield in the 1990s syndicated teen drama "Sweet Valley High" and her portrayal of Kelly Pitts on the CW/BET comedy-drama series "The Game."
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.