Building on recent explorations of humor and improvisational play, this article delves into the therapist’s use of state-sharing that is leavened with humor within now moments as defined by the Boston Change Process Study Group. It explores the role of state-sharing humor in containing, organizing, and interpreting bad object relational experiences and their associated affects within the clinical opportunities that exist in moments of heightened affectivity. The therapeutic elements of state-sharing humor are described, along with affective and relational agility, which are discussed as essential clinical skills in a relational reconceptualization of evenly hovering attention. I link these forms of agility with implicit relational knowing and discuss them as central to the therapist’s capacity to apprehend fragmented and unformed parts of the patient’s self. Clinical vignettes illustrate the therapist’s use of state-sharing humor within improvisational play. These vignettes are interwoven with theory that draws from psychoanalytic relational theory, developmental psychology, and cognitive neuroscience. They demonstrate how state-sharing with humor can generate mutualizing moments of meeting that promote mentalization and launch interactive forms of affect regulation. I suggest that these processes can enable functioning on a subjective level and open up new and enlivening relational experience. (PsycINFO Database Record (c) 2019 APA, all rights reserved)