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The Free Press
The Perils of the Situationship
The Perils of the Situationship
(Illustration by The Free Press)
A 23-year-old straight guy messaged a bunch of women on Snapchat who all found out about each other, and now they’re acting like they’re in the First Wives Club.
By River Page
03.21.25 — Culture and Ideas
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The Free Press
The Free Press
The Perils of the Situationship

It’s been a tumultuous week for 23-year-old Harry Sisson. The DNC’s favorite Gen Z influencer came to mainstream prominence for his adoration of ailing President Biden, who Sisson called “an amazing man and amazing leader.” He brushed off concerns about the president’s mental decline as being manufactured and not a real issue.

Born in Singapore and raised in Ireland, he somehow became one of the Dems’ most high-profile young defenders. Last year, he gained nearly 2 million followers on TikTok, appeared on cable TV news, and was profiled in The New York Times. He stood out because many online men his age are moving decidedly to the right; he’s no left-wing Rogan, but at least he’s something.

But now, Sisson has come under fire—and not just from the Navy SEAL who is credited with killing Osama bin Laden and who once bizarrely suggested he’d keep the rosy-cheeked youth in sexual slavery were it not for the internet. In the last week, 11 women came forward on TikTok to accuse Harry of the unthinkable: flirting with them via Snapchat, simultaneously.

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River Page
River Page is a reporter at The Free Press. Previously, he worked as a staff writer at Pirate Wires, covering technology, politics, and culture. His work has also appeared in Compact, American Affairs, and the Washington Examiner, among other publications.
Tags:
Culture
Love & Relationships
Democrats
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