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Jerry Seinfeld and Shoshanna Lonstein

Jerry Seinfeld was at the peak of his success while starring in his iconic TV series, “Seinfeld,” and had his pick of ladies – not that there was anything wrong with that. However, the one who caught his eye in Central Park in 1993 was Shoshanna Lonstein – who was just 17 and a senior at the private Nightingale-Bamford School in Manhattan. Seinfeld, who was 38 at the time, and Lonstein embarked on a five-year relationship during which he openly gushed about his young love, calling her "the most wonderful girl in the world” and addressing the age issue by saying, “Shoshanna is a person, not an age. …We just get along. You can hear the click." But not long after she moved to Los Angeles to attend UCLA and explore their relationship, they called it quits. Lonstein, now a fashion designer, later told Details, “I felt like I was losing myself” by dating Seinfeld, who she called a workaholic. “I mean, school's fine, but you need more. And there wasn't much else. So I worked out a lot." Seinfeld went on to marry his current wife, Jessica, in 1998, but that relationship was not without controversy either. They met weeks after Jessica had married someone else. She then quickly filed for divorce and started dating the famed comedian.