This paper outlines a self-psychological approach to working with men who please too much. These men feel stuck in enacting patterns of compliance and defiance. Because they feel required to please others, they resort to addictive acts of substance use and unfaithful sexuality to break out of their deadening accommodation and to express their disavowed rage and their thwarted ambition. Reviewing an illustrative case, the author demonstrates how empathizing with each side of these mens' “split selves” and reaching for their disavowed affect facilitates a process of self-integration that improves their ability to assert themselves. Here, the patient responded to the therapist's sustained empathic inquiry by experiencing this disavowed affect and better understanding the meanings of his addictive behavior. His increased self-understanding enabled the therapist to make a momentum-building interpretation that fostered the patient's integration and his willingness to depend on the therapist for self-regulation.