According to attachment theory, insecure individuals respond to events in their romantic relationships in ways that sometimes can be destructive. The objective of this research was to examine how these responses may accumulate over repeated interactions to influence the quality of the relationship. Across three studies, participants were presented with a “Choose Your Own Adventure” dating story in which they made choices based on their partners’ behaviors. In each study we found that attachment styles predicted the kinds of choices participants made at the outset of and throughout the story. Additionally, relationship satisfaction was related to the choices participants made throughout the fictional narrative, even in situations in which the partner’s behavior was the same for all participants.