Jerry Seinfeld’s 17-Year-Old Girlfriend Saga Resurfaces After Duke Walkout

Jerry Seinfeld’s problematic relationship with a high schooler (when he was well into his 30’s) has been grossing out a new generation this week, just after Duke students staged a walk out in protest of his commencement speech.

According to video of the incident that’s making the rounds on X, Seinfeld’s introduction to Duke University’s commencement stage was interrupted by a handful of students who chanted “Free Palestine” and walked out in protest. This comes after campus protests swept the country, as students demanded that their universities divest from Israel amid the country’s attack on Hamas.

Seinfeld has vocally supported Israel and was previously photographed while visiting a West Bank military camp with his family in 2018. According to Times of Israel, the camp posted the photos of Seinfeld on Facebook with the caption, “Finally we are allowed to tell you! Jerry Seinfeld and his family were in Caliber 3. During their visit to Israel last week, they came to us for a special and exciting activity with displays of combat, Krav Maga, assault dogs and lots of Zionism. It was great.” The photos have been making the rounds on social media and receiving renewed interest amidst the Hamas War. Seinfeld returned to Israel to visit with families of hostages taken by Hamas to Gaza last December.

While students at Duke’s commencement walked out to protest Seinfeld’s support of Israel (and likely of his wife Jessica Seinfeld’s funding of anti-Palestine counter-protests this month), these have not been the only points of interest in the spreading dislike for the comedian.

In conjunction with those military camp photos, a quick X search will bring up numerous tweets that reference Seinfeld’s teenage girlfriend from the 1990s, Shoshanna Lonstein Gruss, who he picked up in Central Park when she was still a senior at the private Nightingale-Bamford School in Manhattan, according to People’s cover story about the pair at the time. Lonstein Gruss, now a clothing designer, dated Seinfeld for four years beginning when she was 17 and he was 38.

The Daily Beast has reached out to reps for Seinfeld, who declined to comment for this story, and Lonstein Gruss, who did not return requests for comment.

According to People in March 1994, sources told the magazine that Lonstein Gruss’ family approved of the match, as Seinfeld whisked her around the country to watch him perform and even to meet his mother. Lonstein Gruss told People, “I would like my life to be normal and just go about being a student,” as she dated the famous comedian, and Seinfeld added, “Shoshanna is a person, not an age.”

“I think it’s serious between them,” Seinfeld’s longtime comedian friend George Wallace said at the time. “She’s beautiful and mature. She’s good for him.”

As this type of normalizing media coverage continued for Seinfeld (the People story said “their relationship sure sounds like fun”), Howard Stern was one of the first public figures to call the comedian out for his romantic interest in a minor. Stern sang a parody song about Seinfeld’s relationship at the Miss Howard Stern New Year's Eve Pageant in 1993, where alongside singer-songwriter Janis Ian, Stern crooned, “Seinfeld’s girl is seventeen / An innocent with double D’s / He saw those breasts and flipped his lid for a real young busty high school kid.”

He also called Seinfeld a “horny, lonely TV geek” and Lonstein Gruss “jailbait” in the song—and elsewhere in the lyrics asked, “Can’t he find girls his age to date?” Ian added Lonstein Gruss had “barely shed her training bra” as she “kisses lips for candy bars.”

At first, Seinfeld denied knowing Lonstein Gruss’ real age when confronted about the relationship during an interview with Stern the following year–but on Stern’s show a month later, he said, “I didn’t realize she was so young.” The relationship continued nonetheless, even as Lonstein Gruss attended college at George Washington University, where Seinfeld would could be spotted strolling through campus with her. Despite Stern’s pushing of the “age issue,” as Seinfeld called it, the two men became friends. Just this past week, Seinfeld expressed his love for Stern while apologizing for belittling his long-running radio show.

A few years later, in a Vanity Fair profile timed to the 1998 finale of his eponymous sitcom on NBC, Seinfeld revealed that he “almost got married” to his much younger girlfriend. “I know everyone looked at that relationship as here’s this rich TV guy and here’s this young, hot girl, but it wasn’t like that at all,” he said. “We were very much in love, but the timing wasn’t quite right.”

Seinfeld met his current wife, Jessica, that same year and the two married in December 1999 when he was 45 and she was 28.

And yet three decades after his relationship with Lonstein Gruss first went public, some social media users are clearly not willing to let it go, as condemnation for “grooming”—the term for when an adult befriends a minor in order to make way for sexual advances once they turn the legal age—has grown in recent years. Even before the incident at Duke, X users were circulating sarcastic Seinfeld support tweets that tell viewers to “Google Seinfeld 17 for more,” which brings up a slew of coverage of the relationship Seinfeld would probably prefer everyone forget.

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