Jerry Seinfeld’s Controversial Dating History: A Look Back at his Relationship with a 17-Year-Old

‘Seinfeld' star and renowned comedian Jerry Seinfeld has found himself in the midst of controversy due to his dating history.

One particular relationship that raised eyebrows was when he dated a high school student while he was 38 years old.

Despite being known for his harmless comedic style, Seinfeld's dating choices have not always been without scrutiny.

In fact, his past includes a rather sordid dating history, including a relationship with a 17-year-old girl before his current spouse.

In the early '90s, at the age of 38, Seinfeld began dating a young girl named Shoshanna Lonstein, who is now known as Shoshanna Lonstein Gruss.

Initially, they referred to their relationship as a friendship that blossomed after meeting in Central Park.

However, their connection evolved romantically once Lonstein turned 18.

Unfortunately, their relationship did not stand the test of time.

Lonstein struggled with Seinfeld's lifestyle, public exposure, and ultimately missed her life in New York City after transferring colleges to be closer to him in Los Angeles.

During that time, the relationship became the subject of jokes, with Howard Stern even making light of it by suggesting that Seinfeld carried a “candy bar on a string” in Central Park whenever young girls walked by.

Some publications commended the couple for overcoming the “age issue,” as Seinfeld himself called it.

In 2019, comedian Jeremy Kaplowitz took aim at Seinfeld during the Schtick or Treat event.

Kaplowitz performed standup in the style of a 1990s Jerry Seinfeld, focusing on his relationship with Lonstein.

He humorously touched on the stereotypical behavior of girlfriends, emphasizing their obsession with math homework and desire to live with older celebrity boyfriends.

Seinfeld's questionable dating choices didn't end with his relationship with Lonstein.

In fact, his current wife, Jessica Seinfeld, was married when they first started dating.

They met in a gym in 1998, a mere two months after Jessica had tied the knot with Eric Nederlander.

Jessica claimed that her marriage to Nederlander was already beyond repair when she and Seinfeld began conversing.

However, Nederlander disagreed and expressed feeling manipulated, misled, and caught off guard by Jessica's infidelity.

He went on to criticize both Jerry and Jessica, stating that they lacked respect for decent values and were well-suited for each other.

These controversies have undoubtedly left a mark on Seinfeld's personal life.

While he may be celebrated for his comedic talents, it is important to acknowledge the complexities and controversies that exist behind the scenes.