Kennedy scion's friends reportedly pitch AOC match — and Schlossberg laughs it off
Friends of failed congressional candidate Jack Schlossberg are reportedly trying to play matchmaker between the 33-year-old Kennedy grandson and Rep. Alexandria Ocasio-Cortez, but Schlossberg told the New York Post he wouldn't stand a chance.
Schlossberg, who managed roughly 10 percent of the vote in his bid for a Manhattan congressional nomination this past June, has been licking his political wounds at his family's Martha's Vineyard home. His unnamed friends, meanwhile, appear to have other plans for him. The New York Daily News first reported that Schlossberg's circle has been trying to finagle a meeting between him and the 36-year-old congresswoman, who recently split from longtime fiancé Riley Roberts.
When the New York Post reached Schlossberg on Monday, the grandson of President John F. Kennedy laughed off the whole thing.
"I respect her a lot, she can do way better than me!"
He followed up by calling it "a silly story." Self-deprecating, maybe. But his pals apparently aren't letting up.
A 10-percent candidate and a newly single congresswoman
Schlossberg's June primary loss wasn't close. Earning just a tenth of the vote in a Manhattan Democratic primary, even with the Kennedy name, is the kind of result that sends a campaign operative straight to the liquor store. Friends say he's been "down in the dumps" ever since, and the matchmaking effort appears to be part of a broader project to nurse his political wounds.
Ocasio-Cortez, for her part, is navigating her own personal upheaval. She and Roberts ended their engagement under circumstances that remain publicly unexplained. The congresswoman told TMZ that being a Republican would be one of her biggest dealbreakers in any future relationship, which at least clears the first hurdle for the lifelong Democrat from Hyannis Port.
Insiders familiar with both described the potential pairing in glowing terms. One unnamed source put it this way:
"Those two would actually get along great together. They believe government is a force of good. They'd at least be good friends."
That quote tells you everything you need to know about the ideological lane both occupy. Shared faith in the expanding reach of government is, in certain Washington circles, the foundation of a beautiful friendship.
Schlossberg's friends see a job angle, too
The matchmaking effort isn't purely romantic. Some of Schlossberg's friends have reportedly floated the idea that a connection with Ocasio-Cortez could land him a position in her New York office, a soft landing for a candidate whose electoral debut went nowhere fast.
That detail shifts the story from lighthearted gossip into something more familiar in Democratic politics: the revolving door between failed campaigns and congressional staff jobs. Lose an election by 40 points, and your friends start working the phones to get you a desk in someone else's office. Accountability for the loss is optional; a government paycheck, apparently, is not.
Ocasio-Cortez herself has a Kennedy connection that predates any of this. While attending Boston University, she interned for Ted Kennedy, Schlossberg's great-uncle. The family orbit, in other words, already overlaps.
Both Schlossberg and Ocasio-Cortez are described as prolific Instagram users who have given voters inside looks at their personal lives. In an era when politicians treat social media like a dating-app highlight reel, it's no surprise their respective circles see a natural fit.
AOC's political brand keeps drawing scrutiny
Ocasio-Cortez remains one of the most visible figures in the Democratic Party, and her personal life has become nearly as public as her policy positions. Her breakup with Roberts created tabloid coverage for weeks, and her TMZ comments about refusing to date a Republican only added fuel.
She has also faced criticism on other fronts. The congresswoman drew backlash earlier for adopting an apparent Southern accent at a Memphis rally, a moment that reinforced questions about authenticity that have followed her throughout her career.
Meanwhile, some on the left have been floating her name for even bigger things. Progressive commentator Hasan Piker has publicly backed Ocasio-Cortez for a 2028 presidential run, dismissing critics within her own party. Whether she runs for the White House or simply keeps her House seat, her personal narrative, breakups, dealbreakers, and all, will remain tabloid currency.
Schlossberg, by contrast, has no office to return to. He proclaimed in June that he is looking for a "soulmate," a statement that now reads less like romantic optimism and more like a man searching for a second act after voters handed him a decisive rejection.
No response yet from Ocasio-Cortez
Notably absent from the entire episode is any comment from Ocasio-Cortez herself. The congresswoman has not publicly addressed the matchmaking reports. Whether she finds the idea flattering, absurd, or somewhere in between remains unknown.
Schlossberg's self-effacing brush-off, "she can do way better than me", is charming enough as a tabloid quote. But it also sidesteps the real question his friends are raising, which is less about romance and more about what a 33-year-old Kennedy heir does after voters tell him, in no uncertain terms, that the family name alone isn't enough.
When your best post-election strategy is having your buddies try to set you up with a congresswoman, or maybe land you a staff job in her office, it says more about the state of Democratic talent development than any primary result ever could.






