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Who is the Oldest Woman to be Leonardo DiCaprio’s Girlfriend?

Memed prolifically, Leonardo DiCaprio has a magic dating number— but have any of his old flames beaten it?

Leonardo DiCaprio as Gatsby raising a toast in The Great Gatsby
Image via Warner Bros. Pictures

Leonardo DiCaprio memes occupy a special place in web heaven. There’s Rick Dalton pointing in Once Upon a Time In Hollywood. There’s the fireworks-backed cheers from The Great Gatsby. There’s the sneaky laugh from Django Unchained

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There’s also the gift that keeps on giving: his incredible dating history. How could the great wits of the web miss the curious pattern of DiCaprio’s love life? 

In August 2022, the world remained utterly unshaken at the news that DiCaprio had split with his girlfriend of four years, Camila Morrone. Many thought the writing was on the wall after Morrone turned 25 on June 16. You see, 47-year-old DiCaprio has a distinct history. 

Morrone is the fourth woman to split with the actor just after turning 25. She’s joined an exclusive club that includes: 

  • Israeli supermodel Bar Refael dated DiCaprio on and off between 2005 and 2011. When they ended their six-year relationship, she was 25. 
  • Before starring in Baywatch, model Kelly Rohrbach dated DiCaprio. They parted ways in 2015 when she was 25.
  • Danish model Nina Agdal was 25 when she and DiCaprio ended their relationship after about a year in 2017. 

That 25-year-old cut-off point is no dystopian sci-fi movie — it’s DiCaprio’s dating history. But has any woman ever managed to break ‘Leo’s Run’ and that definitive barrier? The actor has plenty of famous exes he split with before they reached 25, including Naomi Campbell and Blake Lively, but has any special lady crossed it? 

Who is the oldest woman Leonardo DiCaprio’s dated?

Actor Leonardo DiCaprio and his girlfriend, model/actress, Camila Morrone watch the Men's Singles final match between Daniil Medvedev of Russia and Novak Djokovic of Serbia on Day Fourteen of the 2021 US Open at the USTA Billie Jean King National Tennis Center on September 12, 2021 in the Flushing neighborhood of the Queens borough of New York City.
Sarah Stier/Getty Images

It’s good news for internet memes, because the answer is… no, none of the women the award-winning actor is known to have dated has been older than 25. 

For the completists wondering about the identity of the oldest woman DiCaprio dated, from the list above, it’s difficult to tell who had been on the Earth the longest at the time they broke up. Sources said DiCaprio and Rohrbach’s relationship ended a few months before the news broke in early 2016. 

However, it looks like the oldest woman DiCaprio has dated is also one of his longest relationships. He and Bar Refael split in May 2011, ending a six-year on-off relationship just one month before her 26th birthday on 4 June. Eleven years on, and the DiCaprio pattern’s still going.