Humans spend much of their lives in conversation, where they tend to hold many simultaneous motives. We examine two fundamental desires: to be responsive to a partner and to disclose about oneself. We introduce one pervasive way people attempt to reconcile these competing goals-boomerasking-a sequence in which individuals first pose a question to their conversation partner ("How was your weekend?"), let their partner answer, and then answer the question themselves ("Mine was amazing!"). The boomerask starts with someone asking a question, but-like a boomerang-the question returns quickly to its source. We document three types of boomerasks: ask-bragging (asking a question followed by disclosing something positive, e.g., an amazing vacation); ask-complaining (asking a question followed by disclosing something negative, e.g., a family funeral); and ask-sharing (asking a question followed by disclosing something neutral, e.g., a weird dream). Though boomeraskers believe they leave positive impressions, in practice, their decision to share their own answer-rather than follow up on their partner's-appears egocentric and disinterested in their partner's perspective. As a result, people perceive boomeraskers as insincere and prefer conversation partners who straightforwardly self-disclose. (PsycInfo Database Record (c) 2025 APA, all rights reserved).