Sandra Sobieraj Westfall
December 16, 2013 12:00 PM

It was a week filled with somber observances of the 50th anniversary of his grandfather’s assassination, but Jack Schlossberg radiated debonair brightness as he played host at a D.C. dinner for this year’s Medal of Freedom honorees on Nov. 20. Noting that it would have been his great-uncle RFK’s birthday, the Yale junior charmed a black-tie VIP crowd headlined by the President and Mrs. Obama. “While we’re on the subject of birthdays,” Schlossberg said with a grin, “you’re all invited to my 21st in New Haven.”

It was a very public – and solo – debut for the youngest child of the very private Caroline Kennedy, who was half a world away, setting up shop as U.S. ambassador to Japan. And Schlossberg nailed it with a jaunty ease reminiscent of his uncle John F. Kennedy Jr., whom he admires. “Jack is very interested in John Jr.’s life,” says a family friend, “and loves being compared to him.” Beyond the lustrous hair and heartthrob brown eyes, the two namesakes of the storied Kennedy family share a grace and humor, say those who know Schlossberg. At Yale the New York City native performs comedy improv in the exaggerated Boston accent of the rest of his clan and writes boyishly witty blog posts (topics include “How to Ask Out Your TA” and “Crush of the Week”). “He’s just Jack,” says a college friend. “He’s proud of his family, but he doesn’t use that in any way.”

Already the call to service embedded in his genes has him working evenings to get certified as an EMT and volunteering for a local public-safety committee. But the verdict’s out on his feelings about Washington. This fall he blogged that the federal shutdown was putting the “over” in government, adding with sardonic cheek: “Proud of you guys in DC.”

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