Virginity--a major adolescent rite of passage--has been explored in the coming-of-age film genre for many decades. This book examines the evolution of teen movies over the past 40 years, posing crucial questions about how film shapes our cultural understanding of virginity. By surveying more than 30 mainstream and independent coming-of-age films from the 1980s to the present, it considers what types of first-time sexual experiences are represented on screen, how they are different for men and women, and whether they are subverting or reinforcing gender stereotypes. Drawing from notable teen movies such as Dirty Dancing (1987), American Pie (1999), Real Women Have Curves (2002), Lady Bird (2017), and Plan B (2021), the book identifies a progressive shift toward more sex-positive and feminist representations of first-time sexual experiences on screen. Each chapter studies how the political climate, sex education policies, and cultural norms specific to each era impact the film's release and its teenage audience.