This study focuses on how potential romantic partners in speed-dating interactions use improprieties to create relational affiliation and thus pursue intimacy. Within speed-dating interactions, improprieties are viewed as potentially relationally constructive, as they allow speakers to display shared cultural understandings about categories of romantic partner or partnerships. Drawing on a corpus of 72 speed-dates involving 24 participants (12 male; 12 female), a sequential discursive approach was used to analyze how two particular types of impropriety, negative category attributions of non-present others and insults to the present conversational partner, were consequential social actions for creating affective mutual affiliation. The general, albeit surprising, finding is that far from being adversarial, improprieties tended to be useful for pursuing intimacy precisely because they presented interactive trouble. Successfully navigating the interactive trouble seemed to increase a subjectively shared sense of familiarity. The study reveals that non-normative (i.e., less polite) forms of social action may serve as preliminaries for intimacy in first encounters between potential romantic partners.