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Hugh Hefner's widow said she thinks it's a "bad look" that the Oscar winner is "getting older," while his girlfriends are "getting younger," before also claiming that DiCaprio, 49, once hooked up with Rihanna at a Playboy mansion party.
Crystal Hefner thinks Leonardo DiCaprio is following in her late husband Hugh Hefner's footsteps.
While appearing on Hit Network's Carrie & Tommy podcast, the 37-year-old -- who was married to the Playboy founder from 2012 until his death in 2017 -- called out DiCaprio, 49, over his reputation for seemingly only dating women in their 20s, comparing the Oscar winner to her late husband.
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View Story"He's turning into the new Hef, right?" Hefner said. "He's just, like, getting older, the girls are getting younger, and I'm like, 'Oh gosh, it's a bad look.'"
The Only Say Good Things author also went on to recall what allegedly went down when DiCaprio once attended a Playboy mansion party, with Hefner claiming that DiCaprio once hooked up with Rihanna, now 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."'
DiCaprio -- who will celebrate his 50th birthday this year -- has become known for appearing to only date women who are in their 20s, with many of his girlfriends being under the age of 25 specifically when he was in a relationship with them. DiCaprio has publicly dated a handful of women -- including Gisele Bundchen, Bar Refaeli, Blake Lively, Erin Heatherton, Toni Garrn, Kelly Rohrbach, and Nina Agdal -- who were all majorly in their early 20s during their time with him.
He dated actress Camila Morrone, 26, in 2017, before calling it quits four years later. The news of their split broke in August 2022, with reports that they split earlier that summer. At the time, fans online noted that Morrone had turned 25 that June.
Following his split from Morrone, DiCaprio was romantically linked with Gigi Hadid. During the time of their on-again-off-again romance, Hadid was 27 and 28, with the model being the oldest girlfriend he's ever reportedly had.
After he and Hadid called it quits for good, DiCaprio moved on with model Vittoria Ceretti. She will turn 26 in June, according to Daily Mail.
