Role-taking is the process of mentally and affectively placing the self in the position of another. This study used a mixed-methods approach to highlight how a traditional sexual script often imposes gendered expectations of role-taking. To explore role-taking within flirtatious exchanges, a sample of college students read a Snapchat conversation and then inferred what each character was thinking and feeling. Hooking up was the most common qualitative theme among the undergraduate participants; however, this theme was more prominent when considering the perspective of the male character, and this expectation was strengthened by the presence of emoji. The male character was expected to be excited or aroused, more focused on social cues—such as their roommate not being present—and to have the female character over to study as a way to pressure her for physical intimacy. The participants were more likely to think that the female character just wanted to study, was anxious or nervous, and was more aware of the male character’s perspective. These findings highlight the complex nature of conveying sexual interest, which often forefronts desire and agency from a male perspective.