Leonardo DiCaprio, other than being one of the biggest names in Hollywood, has quite a reputation for never settling down and always dating ridiculously stunning women. He definitely has a type, although he does make an exception every now and then. Here’s a comprehensive list of Leo’s past flings and girlfriends.
Danish beauty Nina Agdal was linked to Leonardo from May 2016. The two would often be seen riding around New York City on the Citi Bank bikes, a favorite pastime of DiCaprio’s. Nina and Leo are no longer together. Agdal is a Sports Illustrated model, Maxim magazine cover model, as well as a Victoria’s Secret Angel. In 2013, Agdal was in that year’s Carl Jr. Super Bowl commercial. In 2016, she moved from Elite Models Agency to IMG Models.
Leo and Erin were seeing each other from 2011 to 2012 – one of the longer relationships he has had. Leo has either fling speed or relationship speed. Erin, yet another blonde model, captured Leo’s eye much like previous women in his life. She was part of the Victoria’s Secret modeling group and was featured on their website as well as their 2008 fashion show. As of 2010, Heatheron is a Victoria’s Secret Angel.
Yes, you read that right, Leo was rumored to have wined and dined actress Blake Lively back in 2011. The couple was seen together in both New York City and Paris, making the rumors very convincing. Lively is now married to actor Ryan Reynolds and has two children. We highly doubt she loses sleep at night over Leo. However, we have to say the two did look good together, albeit briefly.
Unlike many of the women on this list, Toni and Leo were actually in a relationship for a while. The two were an item from 2013 to 2014 and were seen all over the world together. Garrn is originally from Hamburg, Germany and got her big break when she signed a contract with Calvin Klein in 2008. She was discovered in 2006 when she attended the FIFA World Cup in Hamburg and was subsequently signed with Women Management modeling agency. She was just 21 years old when she began dating Leo.
We don’t know much about the French national, Margarita Gauchet, but we do know that she was one of the many women who was said to have been with Leo DiCaprio. In 2012, Margarita and Leo were spotted kissing on board a yacht – his usual MO. Leo loves borrowing his friends boats and cruising around various countries around the world. He has been known to be on board yacht much of the summer months.
Going way back here, Leo was seen with Anne back in 2009 whilst the two were frolicking in Ibiza together. The Russian model is known for being a part of the Victoria’s Secret Fashion Show, as well as several Sports Illustrated covers. Anne was also linked to Maroon 5 frontman Adam Levine who she was seeing from November 2011 through March 2012. Anne has since gotten engaged and has had a child with her fiancé, Adam Cahan.
Yes, Leo has been rumored to have had a fling with singer Rihanna and there were photos to prove it. The headlines were made in 2015 and quickly disappeared but nonetheless we were intrigued. Rihanna came onto the music scene in 2005 with her debut album, Music of the Sun, followed by her 2006 album, A Girl Like Me. Today Rihanna is linked to other artists such as Drake and was formerly in a relationship with singer Chris Brown.
Another day another blonde model. Natalie Denning stated that she had engaged in a fling with Leo upon meeting him in Paris back in 2003. Whether this is true or not remains to be seen since she may have used his name to get ahead, but she certainly fits the profile. Denning is an English model who is known for her nude modeling in addition to cameo appearances in productions.
Continuing on the blonde band wagon, Leo dated model Bridget Hall in 1994 when the two were living in New York City. Hall is a model and an actress and has been in productions such as The Devil Wears Prada and has been on the cover of the Sports Illustrated Swimsuit Edition four years in a row. Hall was discovered when she was just ten years old and the rest was history for her as she grew to stand at 5 foot 11!
Going on and on the blonde model front, Leo was said to have been dating model Kat Torres in 2013. Leo really does have a thing for tall, blonde, models. Kat is originally from Bahia, Brazil and is in her late 20s. Another thing Leo likes in his women – that they be young. Like we said earlier, he did make the occasional exception from his usual preference every couple of years. We can only guess so he is kept interested.
Do you remember Trishelle from The Real World? Don’t feel bad if you don’t, most people can’t either. Trishelle is the classic case of good looking woman come to Hollywood after her 15 minutes of fame were up and did everything she could to make it happen. Trish said that she hooked up with Leo. We have to take her words with a grain of salt. Sorry Trish.
We would consider Helena to be the most famous model that Leo has ever dated since Helena is an icon, not just a model. It was rumored that Helena and Leo were an item for a short while during the aftermath of the Titanic fame shoot in 1997. We personally think that is when Leo looked his best too so it makes total sense. Helena has continued to wow the world of modeling and business.
Katie and Leo were caught on camera in 2014 in Cannes. Katie had filed for divorce from her husband of four years a few weeks earlier. Katie, a model and actress, has been in productions such as Iron Man 2, How to Get Away with Murder, Two and a Half Men, and American Housewife. It was said that her husband at the time saw the photos of Katie with Leo and that is what threw him over the edge. Her husband had taken his own life weeks later.
We know Brittany Daniel from her starring role on the teen show Sweet Valley High. She costarred with her identical twin sister on the show as well. Brittany met Leo on the set of their film The Basketball Diaries back in 1995 and it was said that sparks were flying. They played lovers on screen and it was easy to tell that the chemistry worked off screen as well.
Leo met Claire when the two were co-starring opposite each other in the film Romeo & Juliet back in 1996. There were those who said they hated each other while there are others who say they had a secret relationship. We lean towards relationship from how nice they were to one another on the red carpet, plus the fact that they worked together on one of the most loving Shakespearean stories to date.
Dark raven, Emma Miller, another anomaly with the blonde regulars of Leo’s life, was said to have been dating the Academy Award-winning actor back in 2011. Emma is also in her early 20s, as is Leo’s preference, and a tall drink of water. Miller was discovered when she was just 16 years old when she was at a Birmingham Clothes Show. Emma is also a fashion blogger as well as a model and has been rumored to have also been with Leo on other occasions as well.
Linnea, much like Natalie Denning, has gone on record as saying that she had a fling with Leo after they met at a part in London back in the late 90s. The model, who is blonde, does fit the profile for Leo’s usual style and we would not be surprised to learn that Linnea was saying the truth when asked about her fling with Leo. DiCaprio is powerless in front of a tall, blonde woman.
Former Victoria’s Secret model, Miranda Kerr, is well known for her marriage and child with actor Orlando Bloom. However, in 2013, Kerr was also spotted with Leo on a date and rumors started flying. Kerr is now remarried to Snapchat CEO Evan Spiegel; the date with Leo not even in her mind anymore. She is one of the only non-blondes on this list of DiCaprio girlfriends. Kerr has been on the cover of many a magazine, as well as the runway throughout fashion week.
Somewhere between Demi Moore’s separation from Bruce Willis and Leo’s relationship with Gisele Bündchen, there was a time (albeit very short) that Leo and Demi were a thing. This is all strictly rumor, of course, but we know that Demi has a thing for younger men since she was married to much younger beau Ashton Kutcher for years. Demi has since divorced Kutcher as well and has been on her own.
Finally, a photo together! Leo and Kristen dated for a little over a year from 1996 to 1997. She was one of the only women to have accompanied him to an event, hence the photo. Most of his other flings go undocumented. Kristen is a model and an actress and is known for roles in productions such as All My Friends Are Cowboys, Dharma & Greg, Hollywood, and Opposite Day.
Kidada was rumored to have been with Leo in the late 90s. We have to say that Leo is in a place of honor with Jones as she has been linked with men like Tupac Shakur (whom she was engaged to at the time of his death), and LL Cool J. Jones is the daughter of renowned musician Quincy Jones and the half sister of actress Rashida Jones. Kidada is an actress, model and fashion designer.
Model and actress Natasha Henstridge was one of the many women Leo hooked up with in the 90s. The blonde model and the blonde actor were a match made in good looking heaven and were said to have been smitten with each other. Obviously it didn’t last, as does every relationship that Leo goes into but it was nice while it lasted. Natasha has moved on to be a part of films like The Whole Nine Yards, and Species.
Eva is one of the higher profile models on here. If she said that she dated Leo for a month then we have no other choice but to believe her, which is exactly what she did. Eva said that her and Leo were seeing one another over the course of one month back in 1998. If you recall, 1998 was a year after Titanic came out and Leo went from average known actor to total fame.
This one is a bit far fetched since we cannot imagine Naomi Campbell capable of being nice to anyone, but it was reported that Naomi and Leo were hooking up back in 1995. Well, she is a model so it could make sense. Naomi is very private about her personal life and is a hard person to get to know. She has kept very busy in her career of model, television producer and fashion designer, among her many other projects.
Adding another well known model into the Leo DiCaprio mold – Amber Valletta. Amber is one of the many models to be said to have been romanced by the actor. We wouldn’t be the least bit surprised if this were true. Amber has ventured into the acting world herself and has been a part of films such as Hitch, Dead Silence, Gamer, and Transporter 2. Amber has been married since 2003 to Christian McCaw.
On the higher profile end of Leo’s flings is his hook up with socialite and reality television star Paris Hilton. The two were said to have been together very briefly in 2000. Back in 2000, we had no idea who Paris was, since then, though, we know all too well. Her reality television show alongside former best friend Nicole Richie, showed us the spoiled side of this ditzy blonde. Hilton has been relatively quiet in recent years as she is trying to be taken more seriously.
Bijou Phillips is known for her wild ways and her talent. She is a model, actress, singer and socialite. Another title we can add to her many is former flame of Leo DiCaprio. Leo and Bijou dated back in 1998 for a short amount of time but it was enough to get the paparazzi working overtime to get a photo, a photo they never really got. These days, Bijou is married to actor Danny Masterson (That 70s Show) and has one child.
We left Gisele for last because she was the most significant relationship Leo has ever been in. Leo and the Brazilian model were together for five years from 2000 to 2005. While Gisele was pre-Bar Refaeli, she was the first long-term relationship Leo had ever been in, and the world was just eating it up! Gisele ended up ending the relationship because she wanted more, and got her happy ending when she married New England Patriot’s Quarterback Tom Brady and had welcomed two children.
Bar Refaeli and Leo were together for five years, one of Leo’s longest relationships to date. There were many who were sure that the Israeli model would be the one to make Leo settle down and get married. The couple met at a party in Las Vegas in 2005 and were on and off for years. Bar is a model, naturally, and has since gotten married to an Israeli businessman and had a child.
The ultimate girlfriend
Magazine GQ took this “one-type” theory one step further. Their photoshop masters decided to have fun with it and created the perfect Leonardo DiCaprio girlfriend. How could they predict what his ideal woman would look like? They simply took all the beautiful ladies he ever dated and blended their faces into one. The result is below.