Kennedy Heir’s Pals Exposed in Plot to Set Him Up With Dem Star

Politics admin September 6, 2026 0 Comments

Kennedy Heir’s Pals Exposed in Plot to Set Him Up With Dem Star

Jack Schlossberg may have lost his congressional bid, but his friends have faith that he can win the heart of New York’s most prominent lawmaker.

Friends of John F. Kennedy’s grandson are attempting to set up a meeting between him and Democratic Rep. Alexandria Ocasio-Cortez, the New York Daily News’ Richard Johnson wrote on Sunday.

Schlossberg, 33, is single and has reportedly been hiding out at his mother Caroline Kennedy’s house on Martha’s Vineyard after losing the Democratic primary to represent New York’s 12th Congressional District to Micah Lasher in June. According to Johnson, his friends are hoping a meeting with 36-year-old Ocasio-Cortez could spark a job offer—or a date.

A representative for Schlossberg did not respond to a request for comment.

Both New York City natives are known throughout the Democratic Party for their social media savvy, using platforms such as Instagram and TikTok to reach voters. Schlossberg, for example, has frequently used his social media accounts to take aim at his cousin, Health Secretary Robert F. Kennedy Jr. And last month, the congresswoman made headlines after publicizing her decision to freeze her eggs—which brought her even more conservative criticism than usual.

The Kennedy scion has kept his dating life private, as has Ocasio-Cortez. Last month, however, reports emerged that the rumored 2028 contender had quietly split from her longtime partner, Riley Roberts, about 18 months ago.

Ocasio-Cortez and Roberts were last seen last seen in public together at the Met Gala in 2021. Roberts, 38, who works in marketing and web development, met the Queens lawmaker when they were both students at Boston University. Their relationship reportedly began during a weekly debate event called “Coffee & Conversations,” where Ocasio-Cortez and Roberts sparred over everything from pop culture to the war in Afghanistan, according to a 2022 biography of AOC, Take Up Space: The Unprecedented AOC.

When asked about Roberts after being approached by a New York Post reporter outside her apartment in Queens, New York, the congresswoman merely said: “I don’t comment on my private life—thank you.”

Sources told Johnson that Schlossberg is returning to the Big Apple after Labor Day and will turn his attention to charity work. Over the summer, he devoted his time to his niece, 2-year-old Josephine, and his 4-year-old nephew, Edwin. Schlossberg’s sister, Tatiana Schlossberg, died late last year of cancer at 35.