Real-Life Romeo: Remembering Leo DiCaprio’s Many Girlfriends

Darren Ryding May 22, 2023

Kelly Rohrbach

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).

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Rihanna

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.

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Nina Agdal

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.

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Ela Kawalec

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).

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Georgia Fowler

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).

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Lorena Rae

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).

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Laura Whitmore

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).

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Camila Morrone

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).

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Gigi Hadid

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?

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