Some might have clutched their pearls after Barstool founder Dave Portnoy revealed in an April 2025 episode of “Drop A Pin” that he was courting 26-year-old Camryn D’Aloia, but it surely would not be the primary time the 48-year-old had been concerned in a significant age-gap relationship. Au contraire, Dave’s love life has been a bit messy since he and his ex-wife divorced in 2017 — and plenty of of his love pursuits have been considerably youthful than him.

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First up is Portnoy’s ex-girlfriend Jordyn Hamilton, with whom The U.S. Solar claimed he had an affair (although this has not been confirmed). Whereas Hamilton’s age hasn’t been revealed, she has beforehand shared a video of herself dated 1997 wherein she could not have been greater than 4 years outdated, so we might guess that, across the time of her relationship, she might have been 24 or 25. As for Portnoy, he turned 40 in 2017. Issues infamously did not pan out properly between Portnoy and the SoulCycle worker, with Portnoy waging struggle on her office after Hamilton allegedly cheated on him and going as far as to promote “Cuckcycle” T-shirts. Guess he was solely mature in a single sense of the phrase, then. 

Within the wake of all of the drama, Portnoy laid low along with his love life for a couple of years. Nevertheless, that is to not say the messiness subsided. In 2021, he was embroiled in a intercourse tape scandal. Once more, his companion was considerably youthful than him, aged 22, whereas Portnoy would have been 44 on the time. Even so, Sydney Raines took to Instagram to share that, whereas the leaking of their intercourse tape was unlucky, there was nothing untoward about it. “Some might not approve of the video content material, but it surely was solely consensual,” she wrote. She additionally shared that she remained buddies with Portnoy. 

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Finally, among the drama in Dave Portnoy’s love life died down, and in the identical 12 months that his and Sydney Raines’ intercourse tape leaked, he went public along with his relationship with Silvana Mojica, which continued till late 2023. The connection was pretty severe, too, with Portnoy even sharing in a single interview with “Adam’s Apple” that marriage wasn’t off the desk. “I am outdated as sh**, so it is like, I would not be courting any individual if I did not assume there was an opportunity,” he stated, including that issues have been going properly and that he’d met the then-25-year-old’s household. 

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Sadly, it wasn’t to be, and in November 2023, Mojica and Portnoy known as it quits. Mojica made it clear that it was Portnoy who’d ended issues in a TikTok, and Portnoy addressed it as properly in an episode of “BFFs,” sharing that it had come right down to them wanting various things. Notably, he additionally rubbished claims doing the rounds that there had been any infidelity main as much as the break up. Additionally noteworthy was his acknowledgment of their ages. “You are stealing her youth a bit bit,” he shrugged, saying it could have been unfair for the connection to proceed when he knew they did not need the identical issues. 

Time will inform if Portnoy’s relationship with Camryn D’Aloia fares higher. They’ve been linked since April 2024, so issues definitely appear as in the event that they’re good. As for the age distinction, talking of age hole relationships normally, Portnoy has stated he does not choose. Granted, he has additionally hinted at some gaps — akin to 19-year-olds with 29-year-olds — being borderline inappropriate. Guess we’ll must see the way it all performs out. 

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