Few of us are good at asking for what we want or at listening to criticism. In this paper, I explore the many reasons why, emphasizing self psychological explanations, while also noting contributions from marital research, systems theory, and other psychoanalytic schools of thought. After a brief introduction, I provide an experience-near discussion of why people have trouble asking for what they want, the dysfunctional ways they try to avoid making themselves vulnerable, and guidelines for more effective self-assertion. I then discuss the related challenges of listening to other people’s criticism, common pitfalls encountered, and mistakes made, and again offer practical suggestions for helping patients to do better. Along the way, I offer case vignettes to illustrate my thinking. Though not usually described in such everyday language, these speaking and listening challenges are central to our daily work as couple therapists.