Conversation is a fundamental human experience that is necessary to pursue intrapersonal and interpersonal goals across myriad contexts, relationships, and modes of communication. In the current research, we isolate the role of an understudied conversational behavior: question-asking. Across 3 studies of live dyadic conversations, we identify a robust and consistent relationship between question-asking and liking: people who ask more questions, particularly follow-up questions, are better liked by their conversation partners. When people are instructed to ask more questions, they are perceived as higher in responsiveness, an interpersonal construct that captures listening, understanding, validation, and care. We measure responsiveness with an attitudinal measure from previous research as well as a novel behavioral measure: the number of follow-up questions one asks. In both cases, responsiveness explains the effect of question-asking on liking. In addition to analyzing live get-to-know-you conversations online, we also studied face-to-face speed-dating conversations. We trained a natural language processing algorithm as a “follow-up question detector” that we applied to our speed-dating data (and can be applied to any text data to more deeply understand question-asking dynamics). The follow-up question rate established by the algorithm showed that speed daters who ask more follow-up questions during their dates are more likely to elicit agreement for second dates from their partners, a behavioral indicator of liking. We also find that, despite the persistent and beneficial effects of asking questions, people do not anticipate that question-asking increases interpersonal liking. (PsycINFO Database Record (c) 2017 APA, all rights reserved)