This book contributes to the wide gap in theorising sexuality education and adolescent masculinities in urban India. It presents an adolescent perspective on sexuality education, looks at adolescent love from the school teachers’ perspective, and tries to understand a teacher’s negotiations with student romance. It unravels the sexual and romantic lives of adolescents and examines the circulation of sexual knowledge and sources of information on sex that adolescent boys in India have access to. This book uncovers the limits of sexuality education by examining State, feminist, Christian, and sexological materials on sexuality education in Mumbai and Delhi. Based on detailed research and narratives from teachers, young men, and women, the book explores adolescent male romance and its affective registers, adolescent male sexual knowledge, and the regulation of romance in school spaces. This book will be of interest to students and researchers of education, sexuality and gender studies, masculinity studies, sex education as well as those interested in education policy, education politics, educational research, and inclusion and special education. Located at the intersection of sexuality studies, education, masculinity studies, and cultural studies, it will also appeal to those working in sexuality education in urban India within the complex web of the middle classes, consumerism, post-feminism, romance, adolescent masculinities, and cinema.