Billings, a 16-year-old third-year student, and Kennedy, a 15-year-old second-year student, met at Choate, an elite preparatory school, in the fall of 1933. Billings as a teenager was 6' 2", weighed 175 pounds, and was the strongest member of the Choate crew. They became fast friends, drawn to each other by their mutual distaste for their strict school. While at Choate, they formed a club and called themselves "The Muckers". The Muckers would pull pranks around the school and even planned to dump horse manure in the school gym, but that fell through after the headmaster found out. Billings' first visit with the Kennedy family was for Christmas in Palm Beach in 1933, after that, he joined them for holidays, participated in family events, and was treated like a member of the family. The Depression had hurt the Billings family financially, and Lem Billings was at Choate on scholarship. Billings repeated his senior year so that he and Kennedy could graduate from Choate together in 1935.