Valletta has been featured on 17 American Vogue covers throughout her modeling career. That’s why it’s no surprise that she attracted DiCaprio’s attention. Allegedly, he saw the Phoenix-born beauty in a magazine in 1997 and made his move. He ordered his people to contact hers and they dated for a few months.
The relationship didn’t last but it’s fascinating to see how DiCaprio’s mind worked. Later, Valletta began her acting career and became popular in movies like Hitch and The Spy Next Door. Not many models make a smooth transition to a Hollywood career but she did reasonably well (via Just Jared).
Phillips is another former model who found herself on DiCaprio’s hit list. She briefly dated the star in 1998 but their relationship didn’t go very far. However, he did have a massive influence on her career because he helped her get a meaningful movie role. DiCaprio introduced her to movie director James Toback and she starred in Black and White.
Since then, Toback received many accusations of being a serial sexual predator so maybe this wasn’t a good thing. Anyway, her time with DiCaprio signaled a career change that lasted for two decades. It’s funny how meeting one person can cause a seismic shift in how things turn out (via Famous Fix).
Czech model Herzigova met DiCaprio in 1998 at the premiere of The Man in the Iron Mask. Allegedly, they had a steamy affair for a couple of months but it was slightly complicated. Herzigova didn’t allow her marriage to Bon Jovi’s Tico Torres to stop her from pursuing the future Oscar winner.
Meanwhile, Leo didn’t have any qualms about sleeping with another man’s wife. Sources described their short connections as ‘brief’ but ‘intense.’ It won’t surprise anybody that she eventually divorced Torres but she remarried. Now she enjoys a life of luxury in Italy with her billionaire husband (via Fame Chain).
Bundchen remains the only one of DiCaprio’s ex-girlfriends to attend an Oscars ceremony with him. It’s easy to forget that she dated him for five years before she made Tom Brady forget about his pregnant wife. This was DiCaprio’s longest relationship since he became one of Hollywood’s biggest stars.
In 2009, Bundchen spoke about her long time with the untamable actor. “We were very young, and we grew together in a lot of ways,” she told Vanity Fair. “We were just not meant to be boyfriend and girlfriend, but I respect him enormously, and I wish him nothing but the best.”
DiCaprio dated many women but Refaeli has a special place in his heart. He had an on-off relationship with the Israeli model for six years because he couldn’t shake his feelings for her. Allegedly they first met when she was about 19, at a Las Vegas party. Finally, they parted ways permanently when she was 25.
Their connection fizzled out because neither of them wanted to commit or settle down. Bear in mind that DiCaprio was almost 40 by then but he wanted to keep living his best life. The Aviator actor decided that there were plenty more fish in the sea and he kept pursuing them as the rest of this list proves (via InStyle).
In 2009, DiCaprio and Refaeli had a break so the actor decided not to waste time. He immediately pursued Russian-American model Vyalitsyna. She made her name in a scorching Sports Illustrated Swimsuit shoot. The pair met in Ibiza and immediately hit it off. They had an amazing time on the Spanish island but it didn’t go much further.
Vyalitsyna continued featuring on Sports Illustrated covers for 10 years. She hasn’t enjoyed much luck in love since her tryst with DiCaprio. She dated musicians, baseball players, and tycoons but these days she’s a single mother. However, her daughter Alaska is the most important person in her life (via Pop Sugar).
In 2011, DiCaprio shocked the world by dating Lively for a few months. This was a complete break from type because he usually dated supermodels. Lively is a beautiful woman but the actress has a girl-next-door appearance. Meanwhile, it was the first time that he was with somebody from his industry.
It’s hard to imagine the pair together now because Lively has a wholesome marriage to Ryan Reynolds. The pair are raising a happy family and appear to be one of Hollywood’s most functional couples. We don’t know what she was thinking because everybody knew DiCaprio’s reputation (via Glamour).
It’s worth remembering that DiCaprio’s life is incredibly busy. He is one of the most sought-after stars in the world with his pick of scripts. Many actors struggle to maintain relationships because of their travel requirements. That’s ultimately why his 10-month spell with Heatherton came to an end.
Heatherton was 23 when they began dating while DiCaprio was 37. The age gaps were becoming increasingly noticeable as he returned to his favorite type of woman. Heatherton said that DiCaprio’s intense schedule was the main reason why they couldn’t sustain a meaningful connection (via The Observer).
DiCaprio doesn’t discriminate when it comes to love because he dates women from around the world. He added Romania to his list of conquests when he met Ghenea. She made her name in Italy as a stunning lingerie model and caught DiCaprio’s eye. They dated for a few months before the inevitable happened.
They lived it up in Australia on Bondi Beach for a short while as they enjoyed each other’s company. We don’t know if they cycled any e-bikes but you can bet it was on DiCaprio’s radar. These days, Ghenea is dating tennis star Gregor Dimitrov and appears to be living her best life (via Sportskeeda).
For a long time, everyone thought that Kerr and Orlando Bloom were a match made in heaven. But the couple eventually broke up and went their separate ways. This immediately raised DiCaprio’s Victoria’s Angel antenna and he pursued her. Allegedly, Kerr thought that the Inception star was perfect for a rebound.
The 30-year-old model was older than most of the women that DiCaprio previously pursued. But he showed that he’s happy to make exceptions in cases of extreme charm and beauty. Kerr possessed both of these attributes and they met a couple of times in 2013. These days she’s in a happy marriage with Evan Spiegel (via E Online).
Torres is the second Brazilian model on this list and dated DiCaprio later in 2013. She gushed about the legendary actor as she described him as ‘amazing.’ Later his representatives denied that they were together but it’s best to take this with a pinch of salt. They’ve issued more denials than any courtroom lawyer.
A glance at the picture above shows exactly what it is about Torres that seized DiCaprio’s attention. The Sao Paulo native said that she met Leo at a festival and they shared the same house. In recent years, Torres attracted negative headlines because she allegedly used manipulation and hypnosis toward young women (via Vice).
There are no prizes for guessing what Garrn’s day job was when DiCaprio added her to his list of scalps. The German Victoria’s Secret model dated him for about 18 months but it didn’t end well. They began seeing each other in 2013 but it fizzled out because of DiCaprio’s nonstop partying (via VN Express).
Most men dream of being with a beautiful Angel like Garrn but Leo isn’t a normal person. She dumped him after he partied with 20 gorgeous women in Miami. That seems reasonable because it wasn’t the most respectful thing that he ever did. Later, she married Alex Pettyfer but they divorced after two years (via US Magazine).
Readers may have finally realized that Leo has a type. Yes, there have been a few deviations along the way but the overwhelming majority of his love interests are blonde, beautiful, and 20-something years old. Add Horner to this list because he became cozy with her in 2014. He met the British model in the UK and the paparazzi captured them together several times.
Horner posed for British Vogue at the tender young age of 17. Now she’s expecting her first child with her new partner, Jack Whitehall. She met the British comedian after her short relationship with DiCaprio fizzled out. Everybody knew that it wouldn’t last forever because it never does (via Sky News).
We should have kicked this list off with a drinking game. Take a swig every time he dates a blonde model in her 20s. Have another if she was a Victoria’s Secret Angel. Finish your drink if they went cycling through New York on e-bikes. Rohrbach was like a walking stereotype because she ticked all of these boxes.
Naturally, DiCaprio became bored and dumped her. This didn’t stop him from kissing her in public and flaunting their enthusiasm for each other. He may break up with them as a form of penance because he wants to torture himself. He refuses to allow himself to stay happy with one partner (via ABC).
DiCaprio and Rihanna are two of the most powerful and charismatic figures in their respective industries. They’re also close friends and have known each other for a long time. Rumors swirled around their relationship status several times but sources indicate that they are flirty friends (via Pink Villa).
The speculation began when they began spending more time together than before. They went to parties at the Playboy Mansion together and also attended Coachella. With DiCaprio’s reputation, it’s not shocking that people thought that something was going on between them.
Leo made waves when the paparazzi snapped him smooching Agdal in 2016. The seven-time Academy Award nominee had unlocked a remarkable achievement. Agdal was the 10th Victoria’s Secret model that DiCaprio dated in his life. That’s insane but some people felt sorry for him because they thought he was lonely.
Many others scoffed at this because they thought if this was loneliness, it looked good (via The Mirror). This was also the second time that the media linked him to the Danish socialite because they allegedly met two years earlier. She didn’t stay in his life for long but she made a strong impression.
There are two things that DiCaprio loves more in this life than anything else. We know that he adores supermodels but he also appreciates Citi Bikes too. It may seem like a strange hobby for one of the wealthiest actors in history but he genuinely enjoys them. We’ve seen him cycle around New York on rental bikes with several girlfriends.
In 2016, Polish-born model Kawalec became the latest model to accompany him on a fresh jaunt through the Big Apple. He recycled his favorite routine of going for a nice meal before taking a leisurely cycle. Meanwhile, they smooched at various points along their ride (via Elle).
It won’t shock anybody to learn that Fowler is another Victoria’s Secret Model. We’re waiting for the day when one of them rejects DiCaprio’s advances. That’s when everybody should move underground because the end of the world is coming. Fowler dated Harry Styles before she dumped him and used Leo as a rebound.
Cameras caught them dancing together in Cannes at a nightclub venue. The pair couldn’t keep their hands off each other that night as they had a great time. These days, Fowler has a child with her restaurant partner and is living a comfortable life. Meanwhile, DiCaprio continues to sow his oats around the world (via People).
2017 saw DiCaprio add another notch to his belt when he dated Rae. His reps denied that they were a couple but the pair spent plenty of time together. She was 23 and he was 46 as the age gaps started to become increasingly questionable. Several publications captured them together in different places around the world.
They snapped him with Rae at a cocktail party in St. Tropez. A couple of weeks later they cycled through Manhattan on city bikes. They also ate together at Park Avenue, one of the Big Apple’s most exclusive destinations. Yes, they didn’t spend long together but they made the most of it (via People).
Perhaps it’s too strong to say that DiCaprio dated Whitmore but he became very close to her. They allegedly spent the night together at his London hotel after the BAFTAs. But the Irish MTV star made waves because she was already dating musician Rory Williams. Whitemore is older than most of DiCaprio’s conquest because she was 30. But he was happy to make an exception.
I promise I didn’t stay in Leo’s room all night!’ she said.’All this attention has not been easy because I am going out with someone.” However, where there is smoke there’s fire and Williams dumped her the following month. DiCaprio broke a couple of hearts with his Casanova antics (via Metro).
DiCaprio made headlines when he began dating Morrone because he was older than her mother. The pair became official when she was 19 years old but they knew each other for several years. That’s not creepy at all but we won’t go into that. Meanwhile, the Argentinian model’s mother dated Al Pacino, one of DiCaprio’s closest confidantes.
In the end, Morrone and Leo broke up because of his massive commitment issues. Now she is working in the movie world as she tries to become a notable actress. Her time with DiCaprio may have helped her career because it raised her public profile. We wouldn’t want to be cynical and say that’s the main reason why she stayed with him (via Life & Style).
Hadid is one of the latest women on DiCaprio’s hit list. The L.A. native is proving there’s still a place for supermodels in the modern world. She has a massive online following and appeared in publications like Vogue and Harper’s Bazaar. Unsurprisingly this was catnip for Leo who can’t resist a stunning model.
One source told US Magazine: “Gigi has no hard feelings toward Leo and she thinks he’s an incredible guy. Their timing couldn’t align, and they’ve decided to go their separate ways.” Desire flickers like a candle but in this case, it didn’t blaze into an inferno. Will anybody ever tame DiCaprio or will he date supermodels forever?