This chapter explores how loneliness and isolation were embedded within popular concepts of male homosexuality in post-war Britain. It examines how politicians, social commentators and the media constructed loneliness and isolation as both a driver for homosexuality and as consequence of homosexuality and explores what challenges these constructs presented to gay and bisexual men in their efforts to find love, community and agency. The chapter argues that the experiences of gay and bisexual men bring new understandings of isolation and loneliness as both an imposed and experienced set of emotions which have been frequently asserted, revised and negotiated. While some men achieved a form of release from emotional and social loneliness, others faced inner conflicts in challenging restrictive cultural norms.