Seinfeld characters in car
Screengrab via NBC

How did Jerry Seinfeld meet his wife?

The controversial start to their relationship.

Comedian, actor, writer, and producer Jerry Seinfeld became a household name in the late 90s when he starred in his self-titled sitcom Seinfeld.

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Although the fictionalized version of Seinfeld had quite the dating roster (Screenrant reports the character dated over 73 women), the real Seinfeld had a much more brief, if not slightly controversial dating life, before settling down with his wife in 1999.

According to Distractify, real-life Seinfeld’s pre-marriage roster includes comedian Carol Leifer, Angela Hickerson, Caryn Treger, Monica Yates, Susan McNabb, Jennifer Crittenden, and Tawny Kitaen, and an infamous relationship with 18-year-old Shoshanna Lonstein, who he dated for four years in his 40s. Most of his known exes worked with him in front of or behind the camera during Seinfeld‘s nine-season run.

@lauraediez

Replying to @senseimilly #greenscreen jerry seinfeld + shoshanna lonstein met when she was 17/ he was 38 and they actually dated about four years ! #jerryseinfeld #shoshanna

♬ original sound – Laura

Jerry Seinfeld met Jessica Sklar at the gym in 1998. She told The New York Times in 2007 that she was going through a difficult period when he approached her on New York City’s Upper West Side. She had just returned from a troubling three-week honeymoon with Eric Nederlander and had promptly begun moving things out of their shared apartment.

@elderordonez

Jerry Seinfeld and his beautiful Wife Jessica Arriving At Ed Sheeran Concert at The Talkhouse In Amagansett Hamptons New York where he is performing this evening (🎥) @elderordonez1 #edsheeran #andycohen #johnmayer #robertkraft #billyjoel #jonbonjovi #jerryseinfeld #christiebrinkley #sailorbrinkleycook #gwynethpaltrow #chrismullin #paulmccartney #stellamccartney #brookeshields #elderordonez1 #amagansett #hamptons #beautiful #people #nyc #photography #photoofthed

♬ original sound – Elder Ordonez

Seinfeld had gone up to her to try and make her laugh and because she really wasn’t in the mood for laughter at that moment she walked away, but he persisted, and she actually laughed. In her interview with The New York Times, she told journalist Allen Salkin that when Jerry asked her out she’d told him it wasn’t a good time for her to be involved with someone. But the then 26-year-old ended up telling him the whole story of her relationship and his compassion struck a chord with her and rumors of their relationship began to spread in October of 1999.

Of course, tabloids enjoyed spreading the story that Seinfeld had broken up Jessica’s marriage and she had left her husband to date the comedian. Jessica put these rumors to rest many years later in her infamous New York Times interview, saying that her prior relationship was over before she even met Seinfeld or returned from her honeymoon, for that matter. She said the truth was much less juicy than the tabloids.

People reports that by November of 1999, the pair was engaged, marrying a month later on Christmas day. Less than a year after they got married they welcomed their first child in November of 2000. They now share three children; Sascha, Julian, and Shepard. At 70 and 52 years old, the happy couple has been married for almost 25 years.


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Jensen is a Freelance Writer at We Got This Covered. She specializes in TikTok and social media content. She is currently pursuing her M.S. in Journalism at Columbia University and has a degree in Foreign Language & Communications Media. Jensen spends way too much time scrolling on TikTok and is grateful for a position that lets her write about it.