Did Jerry Seinfeld really date a 17-year-old when he was 38?

Jerry Seinfeld‘s been outdated for a good few decades now, but there’s no telling him that. The comedy legend meets any pushback aimed his way with a cantankerous rant about how comedy’s changed.

He’s not wrong about the changing state of comedy, but he is wrong to always point the finger someone else’s way. Sure, the same humor that litters nine seasons of Seinfeld is still occasionally relevant today, but humor evolves. When comedians don’t evolve with it, they become a dying breed.

As he rings in his 70th birthday, Seinfeld is once again showcasing the ego that helped make him one of comedy’s best-known figures. He blames “PC crap” and left-leaning ideals like *respecting other people* for ruining comedy, but its clear comedy has just left him behind. After decades of contributing to the medium, I’m sure its a tough blow for Seinfeld, but its also a part of life.

Seinfeld is aging, and with that process comes a certain degree of reminiscing. His heyday passed a long time ago, but when he was in the thick of it he was at the top of the comedy game. He leveraged that popularity into a flourishing career, a stacked bank account — and a relationship with a woman two decades his junior.

Jerry Seinfeld’s teenage girlfriend

A huge number of people date high schoolers. It’s a completely normal dating practice, so long as you fit one vital criteria: You, too, must be a high schooler. Once you’ve left the halls of your teenaged prison behind, it becomes more inappropriate with each passing year for you to be sniffing around the underaged inhabitants of secondary school.

Did that stop Jerry Seinfeld from donning his creep hat back in the early ’90s in order to date a literal teenager? No it did not, resulting in a relationship between the then-38-year-old Seinfeld and 17-year-old Shoshanna Lonstein.

The pair started dating while Lonstein was still in high school, after meeting in a public park. Seinfeld, apparently unconcerned with an age gap that could easily make him Lonstein’s father, shot his shot, got her digits, and secured a date. One date became many, and soon the pair were an item.

News reports at the time did their utmost to downplay the massive, 21 year age gap between Lonstein and Seinfeld, but even then there was an uncomfortable distance between the two. These days, looking back on the relationship in retrospect, it’s downright stomach-churning.

Seinfeld and Lonstein dated for right around four years, from 1993 to 1997, before breaking up right in the midst of Seinfeld’s high period. Lonstein cited a variety of reasons for the breakup, but largely pinned blame on the incessant press coverage and distance from her hometown and family.

A decade after she started dating Seinfeld, Lonstein married the much more age-appropriate Josh Gruss. By that point she was in her late 20s, and she tied the knot with the Gruss & Co. partner — who is only two years her senior — in 2003. They share three children between them, born between 2005 and 2012, and by now that long ago relationship with Seinfeld is likely little more than distant memory for the writer and fashion designer.