September 9, 2026

Kennedy scion's friends reportedly push AOC matchup — and Schlossberg laughs it off

Friends of failed congressional candidate Jack Schlossberg are reportedly trying to arrange a meeting between him and newly single Rep. Alexandria Ocasio-Cortez, but the 33-year-old Kennedy grandson says she's out of his league.

Schlossberg, who pulled roughly 10 percent of the vote in his bid for a Manhattan Democratic congressional nomination this past June, has been holed up at his family's Martha's Vineyard home since the loss. Now, unnamed pals are apparently working behind the scenes to set him up with the 36-year-old congresswoman, whose split from longtime fiancé Riley Roberts made headlines at the end of August.

The grandson of President John F. Kennedy waved the whole thing off when the New York Post reached him on Monday. His two-word verdict on the rumor: "What a silly story."

Then he offered a slightly longer take:

"I respect her a lot, she can do way better than me!"

Self-deprecating charm runs in the family, apparently. But the matchmaking chatter, first reported by the Daily News, says more about the state of both Democrats' careers than it does about any actual romance.

Schlossberg's 10-percent showing left friends scrambling for a Plan B

Schlossberg entered the Manhattan congressional race banking on the most famous surname in Democratic politics. Voters were unimpressed. His roughly 10 percent finish in June ended any near-term electoral ambitions, and people close to him describe the Kennedy heir as "down in the dumps" ever since.

That same month, he told People magazine he was looking for a "soulmate." His friends, it seems, decided to take the search into their own hands.

An unnamed source described as an insider familiar with both Democrats told the Post that the two would hit it off. The source's reasoning leaned more ideological than romantic:

"Those two would actually get along great together. They believe government is a force of good. They'd at least be good friends."

At minimum, the source suggested, a connection with Ocasio-Cortez might land Schlossberg a job in her New York office, a consolation prize for a man whose own campaign went nowhere. Whether AOC has any interest in hiring a Kennedy who couldn't crack double digits in his own primary is another question entirely.

AOC's breakup opened the door, but her dealbreakers narrow the field

Ocasio-Cortez's split from Roberts, her longtime fiancé, became public at the end of August. The reasons for the breakup remain unclear. But the congresswoman, who has been climbing in national Democratic prominence, has already laid down at least one dating rule: she told TMZ that being a Republican would rank among her biggest dealbreakers.

Schlossberg clears that bar, at least. Both he and Ocasio-Cortez share a family connection to the late Ted Kennedy, Schlossberg as Kennedy's great-nephew, and Ocasio-Cortez as a former intern in Kennedy's office during her time at Boston University.

The two are also described as prolific Instagram users who give followers inside looks at their personal lives. Whether that shared habit amounts to compatibility is a stretch even the unnamed sources didn't try to make.

A Kennedy name couldn't buy a congressional seat, so friends are shopping it elsewhere

The broader picture here is less about romance and more about a political dynasty grasping for relevance. Schlossberg carried one of the most storied names in American politics into a primary and walked out with a single-digit result. His friends' response was not to rethink the strategy but to try networking him into the orbit of a sitting congresswoman, one whose own political future faces its own skeptics.

Ocasio-Cortez, for her part, has not publicly responded to the matchmaking rumors. Her office has not commented on whether Schlossberg is being considered for any staff position. And the unnamed "insiders" driving the story remain just that, unnamed.

Schlossberg himself seemed content to let the whole thing die with a laugh. He dismissed the story, complimented the congresswoman, and went back to Martha's Vineyard.

Ocasio-Cortez, meanwhile, has her own complications. Her socialist credentials have drawn scrutiny from her own base, and she has faced accusations of adopting a fake accent on the campaign trail. Whether she needs a Kennedy on her arm, or on her payroll, is a question nobody outside Schlossberg's friend group appears to be asking.

When the best your friends can do after a 10-percent primary finish is try to land you a date with a congresswoman, the problem isn't your love life, it's your résumé.

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