Continuing to reside in Cambridge, he affected the appearance of an 1890s Edwardian dandy, similar to that of the British Teddy Boys, was a successful racetrack bettor and lived what was described as a Bohemian lifestyle. In 1963, while at his therapist's office, he met Radcliffe student Edie Sedgwick and when, upon turning 21 in 1964, she moved to New York, he went with her and began acting as her promoter.
He continued living in Cambridge, adopting an Edwardian dandy appearance, was successful as a gambler, and lived a bohemian lifestyle. In 1963, while at his therapist's office, he met Edie Sedgwick, a Radcliffe student, and when she moved to New York in 1964, he followed her and became her promoter.