The Gossip Reading Club: Issue One - That Time Jerry Seinfeld Dated a Teenager

When Jerry met Shoshanna and People Magazine thought it was great!
Kayleigh Donaldson
Apr 09 2021
6 min read
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Welcome to issue one of the Gossip Reading Club. To kick things off, we’re starting with something pretty short but sure to spark some interesting conversations.


People. "The Game of Love." March 28, 1994. Karen S. Schneider.



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Read the piece here.


In 1994, Jerry Seinfeld was unimpeachable. His record-breaking sitcom was in its fifth season and consistently pulling in around 29 million viewers every episode. While it would be a few years before the show finished its run at the top of the ratings, a feat accomplished by no other American series since The Andy Griffith Show, Seinfeld's status in history was secure. The man himself was everywhere too, a tabloid favorite and seemingly universally beloved figure. His love life didn't attract Brad Pitt levels of public intrigue but he was certainly making headlines (and would continue to do so when he met his now-wife Jessica after she'd returned to America from her Italian honeymoon with one of the Nederlanders.) But, of course, that's not what we're here to discuss. You know what's coming.


In 1993, Seinfeld met Shoshanna Lonstein. He was 38. She was 17, a high schooler still living with her family. As People said in the 1994 piece we're going to discuss today, "it could have been a skit on Seinfeld": the everyman male comedian pushing 40 and the schoolgirl who "captured his heart."


There is, dishearteningly, nothing new or especially surprising about seeing older male celebrities date far younger women. Leonardo DiCaprio is so consistent with his refusal to be in a relationship with a woman over 25 that people have made graphs to show his pattern of behavior. While researching this piece, I found numerous stories relating to Scott Disick's relationship with Amelia Hamlin, who, at 19, is half his age. Perhaps that's why the People piece veers between humorous shock and questioning sweetness. Once you see the title “The Game of Love”, you know this won’t be especially probing into the obvious power dynamics at play.


The piece opens with an explanation as to how Seinfeld met and first wooed Lonstein when she was 17. Once they began to chat, what he describes as "the age thing" was forgotten. That sort of euphemistic language is all over this piece. Lonstein's youth is downplayed or excused. "She's not 17, definitely not," Seinfeld first insisted to Howard Stern. "I didn't realize she was so young," he claims. A source claims that Shoshanna is "very mature" and the comic insists that “Shoshanna is a person, not an age." I think a lot of women will be painfully familiar with this line of conversation. How many times have you heard a young girl described as being "so mature for her age"?


Re-reading this piece for the newsletter reminded me of Tavi Gevinson's recent piece on Britney Spears, an invigorating essay that cuts through the crap and exposes the shoddy theatricalities that kept young women like Spears smothered by so-called empowerment tactics wielded by powerful men. As she so succinctly put it: "If you can still be considered “mature for your age,” you are not an older person’s equal."


Seineld was joked about in the press and on talk-shows for dating a teenager. Spy Magazine targeted him regularly with snapshots joking that he was heading off to Lonstein's "Sweet Sixteen" and referred to her as a "legal voter" once she turned 18 (by the way, if you want a great time waster, a whole bunch of issues of Spy are available to read in their entirety on Google Books. There's a JFK Jr. piece I'm keen to add to the reading club list.) Of course, he never faced any thorough pushback for it. This People piece feels like a clear attempt to quash the cynicism (and serious questions over him preying on an adolescent girl still attending high school) by playing up the notion that this is true love. It's not just that they're a real couple: they're made for one another, and how could anyone want Jerry Seinfeld to be unhappy?

The piece lovingly details dates at a Los Angeles deli followed by shooting hoops in the park. He buys her clothes from Armani and Ralph Lauren. Lonstein's parents "have always approved of the romance," although they're not quoted here directly. Even Seinfeld's mother is thrilled. Lonstein is positioned here as a real guy's gal, who loves to just hang out with her boyfriend and not be a drag on his time or space (mostly because she's at college.) Mostly, her status her is to be good for Seinfeld, to be there for him. It's portrayed in this piece as being almost chaste, which feels like a deliberate choice given, you know, all of this shit. It even ends with this curious quote:


"As for Seinfeld, he seems serene, a man whose conscience is as clean as his Nikes. “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.”"


Yes, there’s really nothing like people having to repeatedly insist they’re proper and that their conscience is clean when justifying their choice to date a high schooler. Totally makes sense.


Seinfeld and Lonstein broke up in 1997, reportedly because Lonstein missed New York City (she had transferred to UCLA to be near Seinfeld, who worked in California) and did not like the press attention. She now works as a creative director of the fashion label Shoshanna, which she founded in 1998. Seinfeld is married to Jessica, a cookbook writer and runs the charity Baby Buggy.


His relationship with a teenage girl doesn't get brought up much these days, although comedian Jeremy Kaplowitz did a hilarious bit as Seinfeld making jokes about dating a teenage girl for a performance in 2019.


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Please discuss the piece in the comments below. I’m still working out how to use this site properly and work out the best way to get a group chat going. I don’t want anything to be limited by time zones or access, but if anyone has any ideas for better ways to get the reading club going, please let me know.


You can hit me up on Twitter at @Ceilidhann.