Researchers interested in cognitive approaches to relational communication have typically sought explanations for how cognition influences the interpretation of social actions. Few attempts have been made to understand how cognitive structures guide action production. This study extends the work of such researchers by demonstrating the relationship of plans to two social outcomes, loneliness and shyness. College students described how they would request a date from a member of the opposite sex and how they would ingratiate themselves to a new roommate. Each plan was judged for its effectiveness (i.e., likelihood of success) and analyzed for the types of actions represented within it. As hypothesized, loneliness and shyness were inversely related to plan effectiveness in the date-requesting domain for males but not for females. Loneliness and shyness were inversely related to plan effectiveness in the roommate ingratiation situation for both sexes. Results are discussed in terms of their implications for theories of planning and action production in social interactions.