When you’re a high-profile entrepreneur running a massive media company, dating someone 22 years younger inevitably becomes public fodder. But Dave Portnoy, the 49-year-old founder of Barstool Sports, isn’t losing sleep over it. In a candid conversation with Us Weekly while promoting his memoir Cancel Me If You Can, he made it clear that the age gap between him and girlfriend Camryn D’Aloia, 27, simply isn’t a factor in their relationship.
“The age thing is never — people always say it to me — it’s never been a factor. I don’t think about it at all when I’m with her,”Portnoy explained. It’s a refreshingly straightforward take in an era where celebrity relationships face constant scrutiny and judgment. He even put their 22-year gap in perspective by comparing it to other high-profile couples with far larger differences—like Bill Belichick and Jordon Hudson, whose 48-year age gap has generated endless headlines.“In terms of age gaps, we’re starting to look more normal compared to a lot of the age gaps out there,”he noted.
What makes their connection work, according to Portnoy, is simple compatibility.“We both love horse racing. We both like the same things. We go out to dinner early. She’s not looking to party or anything.”It’s the kind of low-key compatibility that rarely makes headlines but is the actual foundation of sustainable relationships. The two were first spotted together at a Boston Celtics and Miami Heat game in April 2024, though Portnoy has since confirmed their relationship publicly.
Beyond the relationship itself, Portnoy also opened up about marriage prospects—a more complicated subject given his ongoing legal entanglement with estranged wife Renee Portnoy. He’s clear that tying the knot again isn’t a priority right now.“I have a girlfriend, she has a boyfriend. If we’re like,‘Hey, we’re getting married,’we’d have to [get a divorce], but other than that, it’s never been a priority,”he explained. He did attempt to divorce previously but the process was denied. His outlook on a potential second marriage is telling:“I’m just happy how I am right now, I guess. I’m not opposed, I don’t think. If I ever get married again, I’ll never get divorced again. I know that.”
The whole conversation reflects a man comfortable with his choices and unbothered by external judgment. In a media landscape obsessed with age gaps, celebrity timelines, and relationship validation, Portnoy’s refusal to treat the topic as controversy is almost defiant. Cancel Me If You Can is out now, offering more unfiltered takes on his life, career, and the culture wars he’s navigated.
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Local Lawton
Local Lawton is a contributor to LocalBeat, covering local news and community stories.