Leonardo DiCaprio‘s dating life has been scrutinized for years now because it has mostly consisted of models who are 25 years old or younger. While no one batted an eye when he was in his 20s and 30s, people are starting to call out his antics since he’s turning 50 this year. His latest critic is someone who understands this Hollywood dating structure very well: Crystal Hefner.
As the 37-year-old widow of the late Playboy founder, Hugh Hefner, Crystal has talked about the imbalance in their marriage. He held all of the power as an icon in the entertainment industry, and she believes that DiCaprio is headed in that same direction if he doesn’t watch it. “He’s turning into the new Hef, right?” She said on Hit Network’s Carrie & Tommy podcast. “He’s just, like, getting older, the girls are getting younger, and I’m like, ‘Oh gosh, it’s a bad look.'”
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In February 2023, there were reports that the Oscar winner was a bit sensitive about people commenting on his then-19-year-old girlfriend, Eden Polani. Even though sources told In Touch that Polani “wasn’t a hookup, just a friend,” DiCaprio was “so upset” because his reputation for only dating women in their 20s started to bug him. “He was venting,” the insider noted. “He was so upset he can’t go out at all without people [thinking] he is dating someone.”
Yet fans are keeping track of who he dates, and there is even a chart that notes their ages. He has an odd pattern of breaking up with women right around the age of 25. There are recognizable names on that graph include Gisele Bündchen, Blake Lively, and Camila Morrone, who were all in their early 20s when they dated him. Recently, after an on-again, off-again fling with Gigi Hadid, 28, DiCaprio has been keeping company with Vittoria Ceretti, 25.
On the podcast, Crystal recalled a DiCaprio story from her days at the Playboy Mansion when she saw him hooking up with Rihanna, 36. “I remember Leonardo DiCaprio and Rihanna hooking up one night,” she said. “I was thinking, ‘That’s smart, hook up with each other, and then they won’t tell anyone.’ ” Perhaps that is some advice that DiCaprio should follow because nobody wants the reputation of being the next Hugh Hefner in Hollywood.
Before you go, click here to see famous men who routinely date women half their age.
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