According to the New York Post, the 33-year-old Schlossberg has been “down in the dumps” since his failed attempt to secure a Manhattan congressional nomination in June, a loss that has left the once-buzzy candidate brooding despite his carefully cultivated image as a fit, media-savvy progressive.
His friends, apparently undeterred by his political flop, are said to be maneuvering behind the scenes to arrange a meeting with the 36-year-old left-wing congresswoman, hoping a flirtation with the Democratic Party’s social media star might soothe his bruised ego and perhaps even revive his stalled career.
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At minimum, these political cupids reportedly believe that a personal connection could translate into professional salvation, speculating that a romantic spark might open the door to a staff position in Ocasio-Cortez’s New York office.
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Schlossberg, however, brushed off the chatter when approached about the idea, responding with a mix of humility and self-deprecation that suggests he understands his diminished standing even within his own ideological camp.
“I respect her a lot — she can do way better than me!” said Schlossberg, who publicly proclaimed in June that he is on the hunt for a “soulmate.”
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His comments underscore the awkward spectacle of a once-promising Democratic hopeful now reduced to tabloid matchmaking fodder, a far cry from the gravitas associated with his grandfather, President John F. Kennedy.
Yet insiders familiar with both lonely-hearted progressives told The Post they reject Schlossberg’s pessimism and argue that his friends may be onto something with their attempted pairing.
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“Those two would actually get along great together,” a source said. “They believe government is a force of good. They’d at least be good friends.”
Both Schlossberg and Ocasio-Cortez are navigating personal and professional turbulence, a shared sense of struggle that some allies believe could form the basis of a bond over wine and sympathetic conversation.
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Schlossberg is reportedly still stung by his dismal 10% showing in the primary and has retreated to his family’s Martha’s Vineyard compound, a classic liberal redoubt, to nurse his wounds far from the voters who rejected him.
Ocasio-Cortez, meanwhile, has seen her private life splashed across headlines after reports that she and her longtime fiancé Riley Roberts had split for reasons that remain murky.
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Both politicians are also heavy users of social media, especially Instagram, where they carefully curate intimate glimpses of their lives in an effort to maintain relevance and connection with their base.
Their overlap stretches back years, as Ocasio-Cortez launched her political journey in the office of Schlossberg’s uncle, the late Sen. Ted Kennedy, where she interned while attending Boston University.
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And in what may be the most important compatibility test for the congresswoman, Schlossberg passes at least one ideological litmus test, as he is not a Republican — a label AOC recently told TMZ would be one of her biggest romantic “dealbreakers.”
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Nevertheless, Schlossberg maintains that Ocasio-Cortez is far beyond his reach, signaling that, for now, the rumored pairing remains more fantasy than reality.
“What a silly story,” he told the Post of claims he might date her, a remark that may disappoint progressive romantics but will likely reassure conservatives who see the entire episode as yet another example of the left treating politics like a social-media soap opera rather than a serious calling.
