This article examines the 1961 diary of a new left young activist to explore his fractured sense of personal and political self. At the height of the Cold War, John Hoyland was an undergraduate at London's University College, living with his Communist Party family and active in the Campaign for Nuclear Disarmament (CND). His intensely political world notwithstanding, Hoyland's diary reveals that interior life troubled his every day and shaped much of his thinking. Hoyland's self-conscious narrative illuminates self-making, male heterosexuality, generation, and relationships and cultures in the early 1960s British Left. He experienced himself as fragmented and struggled to negotiate his conflicting identities. He felt torn between older models of socialist identity and morality, his hedonism associated with the beatnik metropolitan scene, and his project of personal self-improvement. His diary offers rare insight into the intimate thoughts and feelings of one New Left young man at a time when political, social, and sexual codes and cultures were in transition before the emergence of feminist sexual politics. The article examines the identities Hoyland held as a socialist, sexual, and domestic male subject; it considers how his emotional world and relationships were shaped by his metropolitan landscapes, consisting of CND marches, Communist Party meetings, urban youth spaces, and the parental home; and it discusses Hoyland as a writer and the sense of selfhood the diary helped to make possible.