This book analyzes men's experiences and perceptions regarding their participation in infidelity and offers a glimpse into the inner workings of their most intimate relationships, as well as the ways men negotiate marriages that fall short of their expectations. Using a sample collected from the online dating service Ashley Madison, this book finds that contrary to gendered social scripts, the men in this study described motivations for outside partnerships that were not rooted in the desire for sexual pleasure or variety. Rather, men described those relationships as an outlet to soothe their bruised egos, receive attention and validation from a romantic partner, and to fight their feelings of emasculation. These infidelities thus provide support and praise, and aid in the processing of complex emotions. This in-depth analysis provides a unique insight into men's experiences of sexuality and masculinity, and will be of keen interest to those seeking to understand male infidelity from a sociological perspective, across gender studies, psychology, counselling, and beyond.