Two studies investigated the effect of expressed interest on individuals’ openness to opposing viewpoints and perceptions of debate counterparts. Participants in Study 1 engaged in an online conversation with a purported debate counterpart who did or did not express interest in the participants’ viewpoint by asking an elaboration question—that is, a question geared at soliciting additional information. Compared to control participants, participants who received a question rated their debate counterpart more favorably, were more willing to engage in future interaction with their counterpart, and acted in a more receptive manner. Study 2 tested the effects of instructions to prepare elaboration questions on listeners’ responses to a speaker offering counter-attitudinal arguments. Preparing questions caused participants to be more open to the idea of having a conversation with the speaker, to make more positive attributions about typical proponents of the speaker’s viewpoint, and to judge the conclusions of the speech as more valid. Theoretical and practical implications of this research are discussed.