Leonardo DiCaprio is one of the most eligible bachelors in Hollywood. He’s insanely good looking not to mention fun and very wealthy. He’s a talented actor in Hollywood and a guy that always has gorgeous women on his arm. Even when he has a girlfriend you have to wonder if it’s even going to last because he’s never been the sort of guy to be interested in marriage or starting a family. He likes his life just the way it is and he has lost a model or two over the years because he wasn’t willing to settle down.
DiCaprio is known to only date models, though he has made a few exceptions over the years like when he was briefly dating Blake Lively. Regardless of how many girlfriends he has had, he is never single for very long. It’s like he just has a trail of women just waiting for their chance to be with him. Of course, they are also gorgeous and stunning women. He’s not exactly someone that has ever been seen with an “okay-looking” girl. It’s hard to keep track of how many Victoria’s Secret models he’s dated. It must be nice to have so many beautiful women at your fingertips. Read on to see the beautiful women that Leonardo DiCaprio has been lucky enough to date. They are all beautiful and glamorous women.
21. Bridget Hall And Leo Were Young And In Love
Bridget Hall was one of Leo’s first girlfriends, certainly his first model. He was just making it onto the scene here in movies like Romeo & Juliet as well as Basketball Diaries. So why did the two break up? It turns out that DiCaprio is the one that dumped her after a night of lovemaking that she found to be very disappointing. That was the gossip that The London Sun was reporting in 1998. Of course, when Hall was questioned about the whole thing she told New York Magazine that “nothing happened” between the two. It makes you wonder, though. We doubt that nothing happened between them because Leo is known as a ladies man. Either way, the two did not last very long and their romance ended. Maybe she just got sick of his constant partying. He’s certainly changed a lot over the years.
20. Naomi Campbell Is A Top Fashion Model
Naomi Campbell is one model that we were shocked to find out dated Leonardo DiCaprio. She is so high maintenance that we couldn’t imagine her with someone who is so laidback. Rumor has it that back in the day the two only hooked up, but things between them fizzled really quick. It probably had a lot to do with her diva behavior. Throwing phones at the help wouldn’t exactly impress someone like Leo. They decided to stay friends however and she is often seen partying with him on yachts throughout the year. He even photobombed one of her photos with 50 Cent. More than 20 years later, the two are still good friends and that says a lot about what a cool guy Leo is. The two were always mismatched, however, and that’s why nothing came of their relationship.
19. Leo Flew Kristen Zang To Visit Him While Filming Titanic
Leonardo DiCaprio was dating Kristen Zang when he rose to massive fame with Titanic. He was rather taken with Zang and many believed that she might be the one. The two dated for two years and Leo would often fly her to the set of the Titanic so that he could see her, often saying that he missed her when she wasn’t around. He’s not the kind of guy that starts gushing about girls, but with Zang he did. “I can’t wait to see her at the end of the day,” he said. “She is the cutest girl in the world!” So, what happened to these two lovebirds. Apparently, Zang wasn’t a big fan of being in the limelight and Leo was a huge star at the time. The two decided to stay friends and are still friendly to this day. He must have a lot of “friends” that his girlfriends have to deal with.
18. Helena Christensen And Leo Partied At Every Nightclub
Another Victoria’s Secret model, Helena Christensen was a model that Leonardo DiCaprio hooked up with during the rise of his Titanic fame. She was before Zang and considered to be a pretty gorgeous woman. She, of course, is considered to be one of the legendary supermodels of her time. He’s dated a lot of supermodels over the years especially when he was young, but they also didn’t last very long either. At the time DiCaprio used to say that they only “partied” together, but those parties seemed to last a long time. Their hookups lasted long enough for many to consider it a relationship but alas like so many others it didn’t last. She spent time with Leo before she got together with Norman Reedus from The Walking Dead. He’s not the first leading man that she has dated.
17. Gisele Bündchen And Leo Travelled To The Amazon Rainforest And Visit Xingu Indians
Gisele Bündchen is easily one of the most beautiful women that Leo has had a relationship with and she may also have been his longest relationship. The two looked amazing together whether they were on the beach or on the red carpet. We all truly thought that this would be the relationship that would be the one for Leo because the two seemed really great together. There were many rumors going around that Gisele wanted to settle down and have children. Leo wasn’t into the whole idea and things started to get rocky between them. They started dating in 2003 and were on again and off again for five years. In the end, the baby drama or whatever was pulling them apart finally ended them completely. Gisele went on to date her quarterback husband Tom Brady and she finally got the family that she was waiting for.
16. Bar Refaeli And Leo Loved Their Sporting Events
Yes, he certainly does love his models and we really can’t blame him. Gisele was probably not impressed when Leo replaced her with another blonde by the name of Bar. Bar Refaeli was the girl that helped mend Leo’s broken heart after his relationship with Gisele ended. She was yet another gorgeous model, so we don’t think that Leo was crying himself to sleep at night. This was yet another relationship that lasted a long time for Leo, longer than Gisele actually. The two dated for six years and again it came as a surprise when they broke up. We really thought that he might actually keep a relationship going. Why can’t Leo seem to keep a relationship going? We don’t think that this guy is ever going to get married.
15. Anne Vyalitsyna Was In Sports Illustrated For 10 Consecutive Years
We never heard of this girl and there’s a reason for it. Their affair was rather brief and ended quickly. His relationship, if you want to call it that, with Anne Vyalitsyna didn’t last very long. Many people considered her to be a rebound from his breakup with Bar Refaeli. You guessed it; she is yet another model. Leo seems to get involved with a lot of rebounds over the years. These two actually hooked up when Bar and Leo were having a break. The break only lasted six months and Anne was in there during that time. It clearly wasn’t meant to be. The two met in Ibiza and it was a whirlwind affair that ended abruptly when Leo decided to get back together with Bar. It must have been a bummer for Anne who finally thought she landed her man.
14. Eva Herzigova Was Married When The Rumors Started
Leonardo DiCaprio has never been opposed to a little scandal in his days especially when he was young. When he saw a woman that he wanted, he went after her no matter what. That’s what happened when he met Eva Herzigova. Look at how happy these two were together and so very cute. Eva Herzigova is, of course, another famous supermodel whose career went to great heights. This was an affair that was under the radar however because Eva was married at the time to Bon Jovi drummer Tico Torres. Talk about scandalous. These two had their love affair and it reportedly lasted for a whole month. Neither of them will admit it however because she was married but judging by the photo these two had some insane chemistry.
13. Blake Lively And Leo Travelled To Verona
Leonardo definitely shocked the world when he decided to pick up with actress Blake Lively in Paris. Leo dating another actress, we just couldn’t believe our eyes but it was true and the two looked so cute together. They were seen riding bikes together and having fun on the yacht which is obviously something that Leo does a lot. Apparently, Leo was quite taken with the starlet, especially since she is very domesticated. She used to bake for Leo all the time and he loved it. A source told US Weekly, “Leo’s never dated a girl who can cook. And he’s smitten!” The two didn’t last very long though, just five months which disappointed us all because they could have made such a cute couple. Lively of course went on to marry her dream guy Ryan Reynolds while Leo went on to date more models.
12. Madalina Ghenea And Leo Met In Australia During The Great Gatsby
Talk about a stunning model; this girl has legs that go all the way up. There is a reason why he likes models; they are considered to be the most beautiful women in the world. There have been a lot of models that Leonardo DiCaprio dated over time that never really lasted very long. For whatever reason, there are only certain girls that he’s willing to go long-term with. He also seems to date more blondes than anything else. After things ended between him and Blake Lively, however, he hooked up for a brief period with Madalina Ghenea, another model. The two met in Australia when he was filming The Great Gatsby and wasn’t he so awesome in that movie? The two, of course, didn’t last very long. It was a brief stint that didn’t even last a month before the two parted ways.
11. Erin Heatherton And Leo Rode Bikes In Manhattan
Leonardo DiCaprio sure likes his blondes; there is no doubt about that. Erin Heatherton is another stunning model that Leo was with for a brief period of time. She is another Victoria’s Secret models and we can see why, she’s stunning. He has dated ten Victoria’s Secret models over the years and that’s saying a lot. There must be a bet running to see how many he’s going to date. Not too many people can say they dated that many beautiful models, but there is just something about Leo. The two did date for almost a year. Despite how beautiful she is and how well they got along, their relationship just didn’t make it. Apparently, it was their crazy schedules that tore the two apart and we can see that with his schedule as well as hers.
10. Toni Garrn And Leo Travelled To Versailles
Another gorgeous model seen with Leonardo DiCaprio, like we said he loves his blondes. It’s always been funny to see Leo with all these stunning and foxy models. Leo is not someone who worries about being in shape. If he has to be for a movie, that’s fine, but then it ends immediately. He’s the kind of guy that regularly rocks a “dad bod,” and the models don’t seem to care. Not that we would either, it’s Leo after all. He’s a super amazing actor and he’s very rich, so it’s easy to see why a girl would be taken by him. These two dated after he broke things off with Erin and they too only lasted about a year. She is also a Victoria’s Secret model and there were rumors floating around that the breakup was caused by a photo that came out of him leaving a Miami nightclub with 20 other women.
9. Kelly Rohrbach And Leo Attended The US Open
Kelly Rohrbach is yet another gorgeous blonde; these girls are all starting to meld together. There is no doubt about it, Leo has some great taste. Kelly is a Sports Illustrated model and that’s saying a lot. The two started dating in 2015 and started the year off showing massive amounts of PDA while riding bikes. Leo has ridden a lot of bikes with a lot of girls. Things seemed serious between the two as he introduced her to all his friends as they partied in the Hamptons. Rumors started flying around that the two were actually engaged and that he had finally popped the question to one of his models. But instead, after a year of dating, the two broke up in 2016. She didn’t seem too broken up about it, though, as she rocked the beach with her cast mates in Baywatch.
8. Rihanna And Leo Were Caught Smooching At A Parisian
This one seems like an odd match, wouldn’t you think? We thought so too. There was a lot of rumors flying around about these two in 2015. Yes, that would be Leo hiding his face from the paparazzi as he’s walking around with Rihanna. The two tried to keep their fling low key, but that didn’t last very long. The two were caught being quite flirtatious together in Paris that January, but rumors indicated that the two were fooling around long before that. Their fling would have happened before he started dating Kelly and of course as we know it didn’t last very long. At the time Rihanna denied any hookup between her and Leo because she said she was too busy to date and if she did the guy “would have to be man enough to live with my schedule and not get scared.” Clearly, Leo was not the man for the job.
7. Kendal Schuler Is An Australian Beauty
You can always tell which girls didn’t stick around for very long and that’s because there are no photos of them with Leo. It’s almost like they didn’t exist. Kendal Schuler did exist, however, and she was one of the models that Leo dated in 2011 after his breakup with Blake Lively. She is an Australian model who made headlines when she started dating the actor. Maybe that’s part of why they do it, to get a bigger name for themselves as some of them certainly don’t last very long. The two broke up however for whatever reason; it was never told. Busy schedules, too many models around, or maybe Leo just didn’t feel the spark like he did with so many others. Who’s to say? All we know is that we can’t believe how many models he has dated.
6. Laura Whitmore And Leo Celebrated In London
Laura Whitmore is quite the scandalous girl and when she had the opportunity to date Leonardo DiCaprio in 2016, she made sure she became single pretty quickly. Like we said when Leo wants a girl he gets her even if she has a boyfriend. During the BAFTAs Leo apparently snatched Irish TV presenter Laura Whitmore out of the crowd at an after party and was, as they say, “all over her.” It must have seemed like a dream come true. At the time, she was dating Rory Williams and she conveniently became single right after the BAFTAs. There were rumors that Leo had invited her back to his room after the party and we would have to assume that she went. When she was questioned about the interaction with Leo at the party, she told Hello! Magazine, “everyone was just having fun – there was a lot of dancing.”
5. Emma Miller Travelled To St. Tropez For Leo’s Foundation Gala
It’s always surprising when we see a brunette that has dated Leonardo DiCaprio as he seems so partial to blondes. In this case, of course, Emma Miller is a stunning woman, so maybe he made an exception to the rule. She kind of has a little Megan Fox quality to her. He’s not usually someone that grabs women from the United Kingdom as well, but he must have been taken with this woman. The two dated in 2009 right after his breakup with Bar Refaeli, she was clearly part of his rebound stage as they were never photographed together. Not only is she a model but she’s also the actress from Made In Chelsea. The two were seen dining together in a restaurant in South Kensington. It wasn’t meant to be however, the two broke it off and he moved on to yet another model.
4. Rumor Has It Chelsey Weimar And Leo Hit Up Nobu In Miami
Chelsey Weimar was only 19 years old when rumors started flying around about her dating Leonardo DiCaprio. Leo is 43 years old after all, but that doesn’t mean that he can’t land a younger woman. If anything, the guy has grown more good looking the older he gets. Don’t we just hate that about guys? The two were together however at Malibu’s Nobu restaurant and they were photographed leaving it and were in his car together. But friends of the star said there was no way that the two were dating. Page Six reported a source saying, “It’s not true. He isn’t spending time with anyone,” adding, “Most of his time lately has been in places like Indonesia, trying to help save the ecosystem.” Well sure but can’t he have someone beautiful on his arm while he’s saving the world?
3. Nina Agdal And Leo Shopped In LA
Nina Agdal was another young model that was recently linked to Leonardo DiCaprio; it seems he’s going younger these days. Nina is only 24 years old, but that doesn’t seem to bother anyone, especially Leo. She’s certainly a beautiful woman there’s no denying that. The two started dating in May of 2016 and were together for almost a year before they broke it off. The two were photographed everywhere and they looked so cute together. But despite that, it didn’t last and we’re not sure why. She is also a Victoria’s Secret model which is, of course, his favorite models of all. They met during vacations in New York and the Bahamas and they were inseparable after that. It’s sad that his relationships always seem to end, but there also seems to be a new girl following right behind the breakup.
2. Leo Helped Bijou Phillips Get An Acting Gig
During his many relationships as a young actor, there were times that Leo dated some actresses. Though at the time Bijou was a struggling actress though it appears as if Leo helped her along with that as well. Back in the ’90s, Leonardo DiCaprio was linked to Bijou Phillips. The two were linked together in 1998 and apparently, he helped her with her career. She is, of course, the daughter of The Mamas and the Papas singer John Phillips. She can thank Leo for getting her the role in the 1999 drama Black and White, sometimes it pays to date a famous actor. The two didn’t last very long however and she moved on to Elijah Wood. She eventually went on to marry That 70’s Star Danny Masterson in 2011. We suppose it all worked out in the end for her and well we know how well Leo has been doing.
1. Lorena Rae And Spent The Day In The Sun On A Yacht
These days, the actor is being linked to the gorgeous Lorena Rae. If you’re not sure who she is, then you might want to check out her Instagram account with her 1 million followers. She’s yet another model and we have to say that this girl is breathtaking. She obviously caught Leo’s eye and he made sure to connect with her right away. Riding bikes all over the city must be a test for Leo to see if girls can handle it as we all know that he is a big fan of public transportation. Rae is 23 years old and the two have been seen dining together and many people are claiming that they “are an item.” Neither of them is admitting to anything yet and when the paparazzi spot them out Leo will hide his face behind his baseball cap. We’ll have to see if this is the relationship that finally takes for the actor.
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