#6: Jerry Seinfeld and Shoshanna Lonstein

Jerry Seinfeld and Shoshanna Lonstein’s relationship started when they met in Central Park. Despite a significant age difference, Seinfeld being 38 and Lonstein just 17, they dated for four years. In the 1990s, discussions on age gaps were less prevalent than today. However, their 21-year age difference raised eyebrows and fueled speculation.

Tabloids were captivated by their romance, capturing moments like Seinfeld picking Lonstein up in a limousine and leaving her school together. Their relationship endured despite the physical distance, with Lonstein in college at UCLA while Seinfeld working in Los Angeles. However, they eventually split when Seinfeld was 42, and Lonstein was 21. Their separation reportedly stemmed from recognizing different life stages.