This article provides a clinically oriented overview of analogue observational methods used in the assessment of problematic social functioning, specifically skill deficits and social anxiety. This article emphasizes role-play assessment methods, the predominant method used in clinical settings. An examination of the psychometric characteristics of analogue assessment methods is presented, followed by a review of procedural and structural considerations that may impact the quality of assessment data. Of special concern are the potential impacts of instructional variables, structured versus ideographic role-played situations, confederate characteristics and behavior, molar and molecular levels of assessment, self-ratings versus clinician ratings of functioning, and physical attractiveness. Finally, published and empirically evaluated analogue observation tests are critically reviewed with an emphasis on features that may impact their utility in clinical practice.