Helena Christiansen
Leonardo DiCaprio and former Victoria’s Secret Angel and beauty queen Helena Christensen began dating shortly after the actor starred in his iconic “Romeo + Juliet” film. Leo was really starting his rise to fame as a Hollywood actor at the time and was actually less popular than Christensen had been. The two shared a short relationship together in 1997 that ended in just about the same manner and time frame as his other relationships. Fans and tabloids hoped that Leo and Helena would last a little longer since the two had shown quite a lot of potential together, but alas, you shouldn’t keep your dating hopes high when it comes to DiCaprio.
Christensen is still modeling and has also become a businesswoman and photographer in recent years. She’s also an avid climate change awareness activist, which means there’s a chance she and DiCaprio might yet cross paths again someday. She has since dated Australian musician Michael Hutchence, popular actor Norman Reedus (known mostly from his role as Daryl in AMC’s “The Walking Dead”), and even the Interpol singer Paul Banks for a total of seven years. Helena is also quite unique in her choice of cars, choosing to exclusively drive a Morris Minors.
Blake Lively
It seems that Leonardo Dicaprio has dated just about everyone in Hollywood, which means that it was bound to happen that some of his exes would eventually marry yet remain in the same Hollywoodian circles. Blake Lively, whom he dated in later years, is just one example of this as she is currently married to the very talented actor Ryan Reynolds and shares children with him. While some would consider this to be an upgrade, we wouldn't want to hurt Leo's feelings, so let's just say we're glad she found someone. Blake was a lot more motherly than most of Leo's previous girlfriends and reportedly used to make him food, something which he was very grateful for. Like anyone would turn down a home-cooked meal made by Blake Lively.
Lively is best known for her role as Serena van der Woodsen in the CW drama "Gossip Girl." She also starred in various other films but is mostly known today for being the wife of Ryan Reynolds. The couple lives with their children in Pound Ridge, New York, in Westchester County. She definitely looks like a classic match for DiCaprio with her long legs, blonde hair, and beautiful eyes. Unfortunately for Leo, part of that match also meant a fairly short-lived relationship, which is exactly what happened between the two.
Gisele Bundchen
One of the only cases where it really appeared like Leonardo DiCaprio might actually finally settle down with someone was during his relatively long relationship with supermodel and activist Gisele Bundchen. Leo dated the Brazilian supermodel from 2000 to 2005 until she decided to break up with him after feeling like their relationship was causing her more harm than good. She claims to have been drinking a lot at the time and doing drugs while living a shallow and depressed life.
Gisele Bündchen started her modeling career at age 14 when she was discovered by a modeling agency and went on to become one of the highest-earning models in the world. Her claim to fame as a model was becoming a Victoria's Secret Angel between 2000 and 2007.
Madalina Ghenea
Shortly after breaking up with Bar Refaeli, Leonardo Dicaprio was quickly found with a new actress and model. This time it was the Romanian beauty, Mădălina Diana Ghenea. Unlike most of his recent exes, this model was actually a natural brunette, which marked quite a different choice in his relatively non-diverse set of romantic interests. The two were seen together while DiCaprio was in Sydney filming "The Great Gatsby," a romantic drama film based on F. Scott Fitzgerald's popular novel of the same name.
Mădălina Diana Ghenea started modeling at just 15 years old as a presenter for Italian designer Gattinoni. She has modeled in various shows all across the world and was the face of the luxury brand Vanitas. The model is fluent in Romanian, Italian, and English, and has even appeared in a couple of films over the past few years.
Alyce Crawford
Many rumors began to appear of a certain Australian model visiting Leonardo DiCaprio's hotel while he was working on "The Great Gatsby" in Sydney, Australia. We're talking about none other than Australian Model and personal trainer Alyce Crawford, who was often seen posing with Leonardo DiCaprio in public. Although the two were never seen doing anything romantic, it was quite clear to everyone that something was going on between them, especially in these chaotic times of the actor's romantic life.
Eventually, Crawford gushed in an interview with the Daily Mail Australia that the two were just acquaintances and never actually officially dated. According to Crawford, Leo was just: "a really lovely guy." An insider told Australia's Daily Telegraph newspaper that the two were going out for about two weeks and would often meet for hookups multiple times every week. She was quite smart in the way she managed to avoid being seen with him in public, as it helped keep everything a secret, although it would have probably helped out her career to have a few romantic pictures with the popular celeb.