Difficult conversations can foster understanding and growth. Yet, many people struggle to initiate these conversations. Although prior work has primarily concluded that this occurs because people lack understanding of the benefits of difficult conversations, here, we tested whether the struggle to have difficult conversations might reflect a self-regulatory conflict. We first descriptively examined whether people characterize difficult conversations as having a structure in which the costs precede the benefits, typical of self-regulatory conflicts. Across diverse samples (laypeople from the U.S., politicians, physicians, university students from Hong Kong), we found that they do (Studies 1a–1d, 2). We then tested whether people psychologically experience difficult conversations as a self-regulatory conflict by testing whether they prefer to have them in the distant versus near future, a prototypical test of self-regulatory conflict (Studies 3a–3b). Finally, we investigated whether people are aware of the self-regulatory nature of difficult conversations by examining their willingness to take up costly commitment devices (Study 4). Our findings shed light on the nature of difficult conversations and point to interventions to promote honesty in personal and professional life.