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.
Bar Refaeli
One of the most public relationships that Leonardo DiCaprio had ever had was with the beautiful Israeli model Bar Refaeli. The two met at a Sports Illustrated party in Las Vegas just shortly after Dicaprio and Gisele Bundchen had broken up their (relatively) long relationship. Perhaps he was somewhat saddened by the relationship's ending and was looking for another beautiful blue-eyed model to replace his previous love with. The two dated on and off from 2005 up to 2011 before officially breaking up their relationship.
Bar Refaeli is perhaps one of the most popular people to ever come from Israel. She is the most internationally successful model to ever come out of the small country and co-hosted the media frenzy that was the 2019 Eurovision which took place in Tel Aviv, Israel. She has two children and is currently married to Adi Ezra, an Israeli billionaire who made his fortune as a businessman. Despite the relationship between DiCaprio and Refaeli being a bit rocky, it was still one of the most popular pieces of news in Israeli tabloids at the time.
Anne Vyalitsyna
Dicaprio and Bar Refaeli didn't have the most stable of relationships. In the six years they had dated, the actor had found himself with various other women that ironically looked almost exactly like his then-on-again-off-again girlfriend. One of these women was Anne Vyalitsyna, a Russian American model who is best known for appearing in Sports Illustrated Swimsuit Issues from 2005 to 2014. They were often seen vacationing in glamorous locations such as Ibiza. The two were mostly a fun fling as Leo eventually returned to Bar Refaeli.
Anne Vyalitsyna was engaged to Adam Cahan, the former Senior Vice President of Yahoo!'s mobile department, but that eventually ended, as well. She has a very interesting life that includes doing marathons and volunteering to help people with disabilities. Vyalitsyna also dated Adam Levine from 2002 to 2011 and used that connection to appear in two of his band's, Maroon 5, music videos, the most popular being "Misery."
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.
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.