The chapter opens with Roth’s 1959 marriage to Margaret (Maggie) Williams, a divorced mother of two from the Midwest Roth met at the University of Chicago. The impact of the marriage on his self-esteem and mental health, and its effect on his early efforts to shape his developing publishing career, receives special attention. But at the same time, while facing personal challenges, he appeared in the Paris Review, began a new friendship with its editor, George Plimpton, and oversaw the appearance of his first book, Goodbye, Columbus. A year in Rome on a fellowship and a new publisher (Random House replacing Houghton Mifflin) furthered his advances, while he also began to teach at the University of Iowa’s prestigious Writers’ Workshop and then Princeton. New friendships with William Styron and Donald Klopfer of Random House, and work with his early editor Joe Fox, soon shaped the direction of his writing. He also started psychoanalysis, necessary to maintain his mental balance as the relationship with Maggie unraveled and a divorce proved to be impossible. The chapter also examines the reception of his first novel, Letting Go.