Various fields have examined the activity of flirting, predominantly based on experimental and reported data; the interactional workings are therefore often overlooked. Based on emails and chats from two Danish online dating sites, this article investigates how users negotiate romantic connections through the flirting strategy of ‘imagined togetherness’, linguistically constructing imagery of a shared future. Using the notion of the chronotope, turn-by-turn analysis demonstrates how users, embedded in the activity of getting to know each other, tenuously communicate romantic interest by alluding to future points at which they might be together. Central to the strategy is a sequential pattern of avoiding closure and thereby preserving the imagery’s implicitness. The article concludes by arguing that while imagined togetherness functions to probe interests and thus protects oneself from potential rejection, it also draws on fundamental dynamics of fantasy in nourishing the excitement of romantic possibility.