Jerry Seinfeld, 39, was photographed picking up his 17-year-old girlfriend from the high school she attended. This image shows comedian Jerry Seinfeld, then 39 years old, with his 17-year-old girlfriend, Shoshanna Lonstein. At the time, she was still a high school student in New York City, and their relationship sparked media attention. The couple dated for several years despite the controversy surrounding their significant age gap and her being under 18 when they first began seeing each other.