Some may have clutched their pearls after Barstool founder Dave Portnoy revealed in an April 2025 episode of “Drop A Pin” that he was dating 26-year-old Camryn D’Aloia, but it wouldn’t be the first time the 48-year-old had been involved in a major age-gap relationship. Au contraire, Dave’s love life has been a little messy since he and his ex-wife divorced in 2017 — and many of his love interests have been significantly younger than him.

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First up is Portnoy’s ex-girlfriend Jordyn Hamilton, with whom The U.S. Sun claimed he had an affair (though this has not been confirmed). While Hamilton’s age hasn’t been published, she has previously shared a video of herself dated 1997 in which she couldn’t have been more than 4 years old, so we’d guess that, around the time of her relationship, she may have been 24 or 25. As for Portnoy, he turned 40 in 2017. Things infamously did not pan out well between Portnoy and the SoulCycle employee, with Portnoy waging war on her workplace after Hamilton allegedly cheated on him and going so far as to sell “Cuckcycle” T-shirts. Guess he was only mature in one sense of the word, then. 

In the wake of all the drama, Portnoy laid low with his love life for a few years. However, that’s not to say the messiness subsided. In 2021, he was embroiled in a sex tape scandal. Again, his partner was significantly younger than him, aged 22, while Portnoy would have been 44 at the time. Even so, Sydney Raines took to Instagram to share that, while the leaking of their sex tape was unfortunate, there was nothing untoward about it. “Some may not approve of the video content, but it was entirely consensual,” she wrote. She also shared that she remained friends with Portnoy. 

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Eventually, some of the drama in Dave Portnoy’s love life died down, and in the same year that his and Sydney Raines’ sex tape leaked, he went public with his relationship with Silvana Mojica, which continued until late 2023. The relationship was fairly serious, too, with Portnoy even sharing in one interview with “Adam’s Apple” that marriage wasn’t off the table. “I’m old as sh**, so it’s like, I wouldn’t be dating somebody if I didn’t think there was a chance,” he said, adding that things were going well and that he’d met the then-25-year-old’s family. 

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Unfortunately, it wasn’t to be, and in November 2023, Mojica and Portnoy called it quits. Mojica made it clear that it was Portnoy who’d ended things in a TikTok, and Portnoy addressed it as well in an episode of “BFFs,” sharing that it had come down to them wanting different things. Notably, he also rubbished claims doing the rounds that there had been any infidelity leading up to the split. Also noteworthy was his acknowledgment of their ages. “You’re stealing her youth a little bit,” he shrugged, saying it would have been unfair for the relationship to continue when he knew they didn’t want the same things. 

Time will tell if Portnoy’s relationship with Camryn D’Aloia fares better. They have been linked since April 2024, so things certainly seem as if they’re good. As for the age difference, speaking of age gap relationships in general, Portnoy has said he doesn’t judge. Granted, he has also hinted at some gaps — such as 19-year-olds with 29-year-olds — being borderline inappropriate. Guess we’ll have to see how it all plays out. 

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