Despite sexual imperatives and social norms marginalizing non-sexualities – referred to as compulsory sexuality –, representations of sexually inexperienced emerging adults (SIEA) in works of fiction have been overlooked. The goal of this research was to document media representations of SIEA in popular fictional television series and movies in a contemporary North American context. We conducted in-depth analyses of fictional television series and movies that portrayed at least one lead or secondary SIEA character. Eleven characters were analyzed through a conceptual framework based on social clock, script, and stigma theories. A hybrid qualitative analysis combining tenets of dialectical team-coding, textual, narrative, and critical discourse was conducted. First, each character was assessed regarding the virginity script it best depicted. Three characters (Anastasia, 50 Shades of Grey; April, Grey’s Anatomy; Jane, Jane the Virgin) fit the gift script, five characters (Shoshanna, Girls; Charlene, F**ked Up; Brian, The Young Kieslowski; Jules, L’heure bleue; Peter, The Late Bloomer) best belonged to the stigma script, and three characters (Kala, Sense8; Chiron, Moonlight; Sam, Atypical) exemplified the process script. However, there was some script overlap in many of these representations, which were found to be insufficient to adequately capture the complexity of each characters’ situation with regards to their sexual inexperience. Second, we developed a matrix in which each character was positioned on four axes: (1) intentionality of sexual inexperience, (2) identity, (3) social skills, and (4) social integration. Third, stigma manifestations of SIEA characters were found at the individual, interpersonal, and structural levels. Gender differences were salient in our corpus: male characters’ inexperience was depicted as a by-product of extrinsic or uncontrollable factors (e.g., medical condition), whereas female characters were held responsible for their inexperience and asked to “justify” it. In fact, gender was the primary characteristic through which characters were represented, and superseded the place given to sexual inexperience in the narratives.