Dave Portnoy, the outspoken founder of Barstool Sports, has never been shy about his personal life, especially when it comes to relationships. But if you’ve been following his dating history, you might have noticed a pattern—or maybe it’s more of a tendency—that his love interests often have a significant age gap compared to him. At 48 now, his relationships have drawn quite a bit of attention, not just because he dates younger women but also because of some messy fallout along the way.
A String of Young Partners and Public Breakups
Let’s rewind a bit. After his divorce in 2017, Portnoy’s dating life seemed… well, let’s say complicated. One of the earliest younger partners publicly linked to him was Jordyn Hamilton, a SoulCycle instructor. Details about her exact age weren’t clear, but she posted a childhood video dating back to 1997 where she looked very young—so it’s safe to guess she was in her mid-twenties during their relationship. Meanwhile, Portnoy had just turned 40 around that time. Their relationship apparently didn’t end quietly either. In fact, things got heated after allegations surfaced that Jordan had cheated on him—allegations he responded to by mocking her workplace, selling T-shirts labeled “Cuckcycle.” It was a pretty public meltdown, which kind of surprised me, considering how composed he usually comes across online.
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After that, Dave seemed to pull back from the spotlight regarding romance for a bit, but it didn’t mean the drama stopped altogether. Fast forward to 2021, and Portnoy was caught up in a sex tape scandal involving Sydney Raines, who was just 22 at the time while he was 44. Sydney publicly maintained the situation was consensual despite the leak and said she kept a friendly relationship with him. It felt like something that could have gone sideways but didn’t totally implode, at least publicly.
Serious Talk and Another Time Around
Later in 2021, Dave started dating Silvana Mojica, who was 25 then—a relationship that appeared more grounded, or at least more serious. Portnoy even opened up during an interview, hinting that marriage wasn’t completely off the table. He told the host he wouldn’t be dating her if there wasn’t a real chance, adding that he’d met her family, which seemed like a big step for him. But, of course, it didn’t last.
By November 2023, things had ended. Silvana confirmed on TikTok that Dave was the one who ended it. Portnoy also spoke about the breakup on his podcast, sharing that it boiled down to them wanting different things in life. He denied any cheating rumors, which he thought were just speculation. What stood out to me was his somewhat candid admission about their age difference. He said something along the lines of “stealing her youth,” which sounded like a rare moment of self-awareness. It seemed like he recognized that, maybe, the gap wasn’t just a number—it affected the dynamic and future of the relationship.
What About Now? New Flings and Opinions on Age Gaps
Dave’s most recent public relationship is with Camryn D’Aloia, whom he’s been linked to since April 2024. She’s 26 years old—still quite a bit younger than him but not drastically different from his previous partnerships. So far, things seem to be going alright between them, but given Dave’s history, it’s hard not to wonder how it will pan out.
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Interestingly, Dave hasn’t ruled out age-gap relationships in general. In fact, he’s quite open about not judging people for dating someone much younger or older as long as it makes sense to both parties. Although, he has mentioned that certain age differences—like between teens and people nearing thirty—can feel off or borderline inappropriate. That’s a nuance worth noting because it shows he’s not blindly endorsing all age gaps but thinking about some boundaries, even if his own relationships sometimes test those limits.
I have to admit, there’s something oddly relatable about this whole saga. People aren’t perfect. They make choices that don’t always add up. And here’s this guy, who’s wildly successful in business, but his personal life is far from smooth sailing. It kind of humanizes him a bit, even if it’s messy.
At the end of the day, only time will tell if this latest relationship sticks or if it falls apart like the others before it. Given the pattern, though, I wouldn’t be surprised if there are still many chapters left to write in Dave Portnoy’s love life.
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