Social scientists and conversation analysts have both focused on advice as a key form of support and influence, but neither have adequately connected patterns of verbal behavior in advice interactions to recipients’ reduced satisfaction with advice. We address this concern with an interpretive discourse analysis of naturalistic "troubles talk" between college student friends. Transcripts (N = 48) were selected for analysis from a larger study of supportive interactions because the recipients in these interactions reported the advice as less satisfying on one or more dimensions, relative to the other advice recipients in the study. Our analysis explicates four trajectories of advice and resistance that characterize these interactions: sustained resistance, advisor persistence, irrational resistance, and contesting the problem. We discuss theoretical and pragmatic implications of these trajectories, including probable influences of the "friend" role on advising interactions, and the responsibility of both advisors and recipients for producing and preventing dissatisfaction with advice.