Amos Kendall was markedly shy. In part, this was due to the lack of social graces taught to him in his childhood and adolescence. He did not actively participate in social gatherings until he moved to Groton, Massachusetts, in 1811. In Groton, he fell in love with 16-year-old Eliza, the sister of a prominent Boston family of merchants. She refused his attentions (as she was too young to marry), and Kendall wooed her older sister, Mary. But the loss of his legal apprenticeship and subsequent move to Kentucky in 1813 ended their relationship.