Dated a 17-Year-Old While in His Late 30s—And Hollywood Let It Slide

In the early 1990s, Jerry Seinfeld—then 38 years old and riding high on the success of his hit TV show—began a relationship with Shoshanna Lonstein, a 17-year-old high school senior he met in Central Park. Their initial meeting reportedly involved her giving him her phone number, and soon after, the two began dating. At the time of their relationship’s start, Lonstein was still legally underage in several U.S. states, and certainly still in high school. Despite the glaring age gap and disturbing power dynamic, the relationship was treated as celebrity gossip, not a red flag. Seinfeld publicly flaunted the romance, and the media largely played along, painting it as quirky or even aspirational. The reality? A 38-year-old man—one of the most famous in America—dating a teenager who hadn’t even finished high school. They dated for about four years, during which Lonstein grew from teenager to young adult under the intense scrutiny of the public eye—while Seinfeld’s behavior barely raised eyebrows in an industry known for looking the other way. The eventual breakup was treated as just another Hollywood split, but the relationship remains a stark example of how fame shields problematic behavior. This wasn't just about “love” or age gaps—it was about power, grooming, and how celebrity status can blur moral boundaries in plain sight.