Jerry Seinfeld, worth $950 million, made headlines when he dated Shoshanna Lonstein, who was allegedly 17 years old when they met. Seinfeld was 38 years old at the time, and there was public scrutiny of their relationship due to the large age difference. Seinfeld defended himself by saying that he didn't know how old she was and that they clicked because she was funny and sharp. They confirmed their relationship when Lonstein turned 18 but broke up four years later due to public scrutiny and distance. Lonstein went on to become a successful fashion designer with a net worth of $50 million.