1993 was a good year for Jerry Seinfeld. His sitcom, which was on its way to becoming one of the most celebrated shows in television history, won an Emmy in the category of “Outstanding Comedy Series” for the first and only time. And, just a hair shy of 40, he met a woman who would capture his heart: a high school student he picked up one day in Central Park.
Shoshanna Lonstein was a senior at the prestigious Nightingale-Bamford School on the Upper West Side when, on a spring afternoon, she was approached by one of the most well-known comedians in the country. It appears unclear if Lonstein knew exactly who she was talking to at the time, but after a short conversation, she gave her phone number to the comedian, sparking a relationship that would begin around her high school graduation and end right after her college one.
The story of Jerry and Shoshanna is probably best told in a People article titled “The Game of Love,” published in March of 1994, which is positioned from the perspective of the world having taught itself to accept their romance. “When Jerry Seinfeld fell for 17-year-old Shoshanna Lonstein, cynics snickered,” the subheadline reads. “No more.”
And yet, the article mostly focuses on Seinfeld’s quest to justify dating a woman 21 years younger than him. Near the very top of the story, People’s Karen S. Schneider recounts an interview Seinfeld did with Howard Stern, in which Stern, as he would, jokes about Seinfeld being the sort of boogeyman in a windowless van that parents warn little children about.
Howard Stern homed in on the May-August aspect of the relationship when the radio host interviewed his old friend last spring. “So,” Stern said, feigning moral indignation, “you sit in Central Park and have a candy bar on a string and pull it when the girls come?”
Amazingly, Seinfeld, master of his comedy domain, was flustered. “She’s not 17, definitely not,” he initially insisted.
Depending on exactly what period Seinfeld is talking about, he might have been telling the truth: Lonstein turned 18 on May 29, 1993, shortly after the two met.
Still, Seinfeld returned to Stern’s show soon thereafter for what Schneider calls “spin control,” though he was still obfuscating the details of their early relationship.
Then, returning to the Stern show a month later for another attempt at spin control, he still seemed a bit defensive. “I didn’t realize she was so young,” he said. “This is the only girl I ever went out with who was that young. I wasn’t dating her. We just went to a restaurant, and that was it.”
It’s sort of hard to tell what Seinfeld meant here when he says he “wasn’t dating” Lonstein. Perhaps he was attempting to draw a line between their relationship when Lonstein was 17—not “dating”—and when she turned 18—“dating.” Regardless, their romance bloomed, and the two became tasty tabloid fodder.
Scans of the People story contain three photos of the couple. In one, Seinfeld and Lonstein—who looks very much like a high school student—appear swarmed by photographers, with Seinfeld wearing a face of quiet but distinct terror.
The other two photos, shot by a paparazzi from some distance, show Seinfeld and Lonstein playing basketball and kissing.
Over the summer of 1993, according to People, Seinfeld would show up at Lonstein’s parents’ apartment and whisk her away:
Within weeks after their first date, friends and neighbors grew accustomed to the sight of the Seinfeld limousine idling outside the Upper East Side luxury apartment building where Lonstein lives with her 15-year-old brother, David, and her parents, Zachary, a wealthy computer-store owner, and Betty, a home-maker.
Soon enough, though, the couple went long-distance—Lonstein was off to college at George Washington University in D.C., and Seinfeld headed back to Los Angeles to continue filming Seinfeld. The two decided to stay together, and on visits she would parade him around campus, while in L.A. he would bring her along to lunch with his famous friends:
For months now, Seinfeld and Lonstein have quietly gone about the business of getting to know one another. At George Washington University in Washington, where Lonstein, now 18, enrolled in September, the couple walk arm in arm across campus when Seinfeld pops in for an occasional visit. On weekend trips to Los Angeles, where he tapes his show, they have eggs and cheesecake with his friends and cast members at Jem’s Famous Deli in Studio City before heading off to spend an afternoon shooting hoops in the park.
He would also fly his young girlfriend around the country on shopping trips—a proper rich man thing to do. The People article, which essentially chronicles the first year of their relationship, continues on with further justifications of the couple’s strange existence from both Seinfeld and Lonstein, as well as unnamed sources “close” to the both of them.
Here is Seinfeld:
“I am not an idiot,” says the comic. “Shoshanna is a person, not an age. She is extremely bright. She’s funny, sharp, very alert. We just get along. You can hear the click.”
And Seinfeld again at the article’s closure, arguing in favor of their relationship being “proper”:
“When I wasn’t involved with Shoshanna and was seeing several women, then it was awkward,” he says. “You go out with one girl and the other sees you with her in the paper. That was uncomfortable. Now I’m not doing anything I’m uncomfortable with. My interest in her is very proper.”
Lonstein is quoted once about the difficulty of dating a celebrity—“I would like my life to be normal and just go about being a student, but these daily obstacles don’t take away from our relationship”—and People also cites “a source close to her family” as saying that her parents approve of their relationship (there is no indication that they didn’t).
Seinfeld also seemed to have the support of his colleagues. Julia Louis-Dreyfus, in an interview in New York in 1999, after Seinfeld and Lonstein broke up, said that she was in favor of the couple because it made Seinfeld happy:
“No, it didn’t make me cringe,” she says. “When he was in that relationship, it was a happy one for him. And she’s a terribly nice person, so I was in favor of it. Come on — who cares? There wasn’t anything wrong with it. I thought it was great. Anyway, they’re not dating anymore, if that gives other people any happiness.”
Regardless of public opinion, the couple survived their first year together, and during the summer after her freshman year of college, Lonstein transferred from GW to UCLA to be closer to Seinfeld. But in December of 1994, 18 months in, People reported that the two had broken up, the reason stated being that Lonstein was bored by Seinfeld talking constantly about work (good reason!). The story also said that Seinfeld proposed to Lonstein, but had angered her when he asked her to sign a prenup:
And, says this source, “she has a temper”—which exploded last month after Seinfeld, according to one tabloid account, proposed marriage. That was fine—but not his follow-up proposal that his fiancée sign a prenuptial agreement. Friends of the couple find that scenario dubious. As one points out, Lonstein, whose father lives in New York City and is president of a successful computer-services company, “didn’t need Jerry’s money.”
Who knows whether that story is true—Seinfeld and Lonstein would continue to date for another three years, so it’s possible that the People’s entire item was bullshit. But Seinfeld did have a history of sudden proposals: in the earlier story about their relationship, People reported that in 1984 Seinfeld had become engaged to a hotel manager “in a moment of panic that hit him when he turned 30” before breaking up with her a few months later.
If Seinfeld didn’t actually propose to Lonstein in 1994, then he might have in May of 1996, when she turned 21. There’s little information about that rumor currently living on the web, but it trickled far enough up that Conan O’Brien made a crack about it on his nascent late night show in June of 96 (via the Chicago Tribune):
“Jerry Seinfeld proposed to Shoshanna Lonstein on the night of her 21st birthday. Apparently he wanted to wait to make sure she wasn’t just using him to buy beer.”
— Conan O’Brien, on “Late Night”
And if the proposal didn’t happen then, it certainly happened at some point. A 1999 post-break up profile of Lonstein in the New York Observer quotes a Seinfeld interview from Vanity Fair in which he says the two were nearly wed:
“We were very much in love,” he told Vanity Fair last year. “But the timing wasn’t quite right. I almost got married to Shoshanna.”
Neither of the two ever seems to have explained exactly why they didn’t get married, though Lonstein was said to always have struggled with the peering eyes of the press. The Observer, which was writing about Lonstein’s successful line of clothes at Bloomingdale’s, had a good hypothesis as well:
Maybe it wasn’t just the timing. “I don’t want my wife to work,” Mr. Seinfeld told the glossy. “I’ve had enough career for both of us.”
In any event, by early 1997, nearly five years after meeting, the two had split for good. Lonstein graduated from UCLA and wanted to return to New York, so she did, leaving Jerry in Los Angeles. In October of 1998, Seinfeld met Jessica Sklar, the woman who would become his wife, at a gym near his apartment in New York. (There was drama there as well: Four months prior to meeting Seinfeld, Sklar herself had gotten married to Eric Nederlander, the son of very wealthy theatre magnate Robert Nederlander. Soon after meeting Seinfeld, Sklar broke off her marriage, and a year later, in November 1999, Seinfeld consummated his second scandalous tabloid romance by proposing to Sklar at Balthazar in New York. “Good luck to her,” the New York Post quoted Sklar’s ex-husband as “sniffing” upon hearing the news of her engagement to Seinfeld.)
Things have more or less gone smoothly for both Seinfeld and Sklar since then. Lonstein, upon moving back to New York, became an accomplished fashion designer, which you can read all about on her thorough Wikipedia page. In 2003 she married a banker named Joshua Gruss, with whom she had three kids before they divorced late last year.
Seinfeld, of course, is obscenely wealthy, with three children of his own by Sklar, although a typically melodramatic National Enquirer story from 2013 offered that perhaps the premiere comic voice of a generation never quite got over his child bride to be:
But pals wonder whether he’s still pining for his ex-flame Shoshanna Lonstein, who was an 18-year-old high school graduate when she started dating Seinfeld, then 39. The two dated for four years before his workaholic ways reportedly led to a breakup.
“It’s also clear he still hasn’t found real happiness and remains somewhat depressed. Pals believe he really never got over his bustup with Shoshanna and wonder if he would be happier today had they been able to make it work.”