Jerry Seinfeld’s Past Relationship With Teenager Resurfaces After He Says He Misses ‘Dominant Masculinity’

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Due to the release of his poorly-received Netflix movie Unfrosted earlier in May, comedian Jerry Seinfeld has been doing tons of press recently and has created quite a few headlines along the way.

Most recently, Jerry Seinfeld made some comments about masculinity in society while appearing on the Honestly with Bari Weiss podcast, saying that he misses the times of “real men.”

“I really thought when I was in that era, again, it was [John F. Kennedy], it was Muhammad Ali, it was Sean Connery, Howard Cosell, you can go all the way down there. That’s a real man,” Seinfeld said.

“But I miss a dominant masculinity. Yeah, I get the toxic thing. Thank you, thank you. But still, I like a real man.”

Seinfeld’s comments about liking a “real man” perhaps haven’t been received as he expected, as it’s largely just caused people on social media to reminisce on that time in the early 90s when he was allegedly dating Shoshanna Lonstein Gruss, whom he met when she was still in high school.

The timeline of Seinfeld dating Gruss when she was a teenager has been fact-checked by Snopes, citing a 1994 article in People Magazine:

“Jerry Seinfeld was strolling through Central Park one day in May 1993 when he spotted a stranger he now calls ‘the most wonderful girl in the world.’ Seinfeld, then 38, sallied over, made small talk and went away with the telephone number of Shoshanna Lonstein — then 17 and a senior at the private Nightingale-Bamford School in Manhattan.”

Many who came across Seinfeld’s comments about “real men” were quick to remind him that no matter what your definition of “masculinity” is, dating a teenager who is 21 years younger than you should certainly never be part of it.

Seinfeld’s latest movie Unfrosted, the first that he’s ever directed, is now streaming on Netflix. In addition to directing, Seinfeld stars in the film alongside Melissa McCarthy, Jim Gaffigan, Max Greenfield, Hugh Grant, and Amy Schumer.