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Successful romantic relationship initiation often requires bold and direct action, but direct action can increase the possibility of rejection. These dual possible outcomes create interpersonal risk, which should prompt self-esteem differences in behavior. When risk is present, lower self-esteem individuals, who prefer to avoid social costs, will be less likely to use direct initiation behaviors than higher self-esteem individuals, who prefer to approach social rewards. However, eliminate social risk and these self-esteem differences in behavior will be similarly eliminated. Furthermore, reflecting gender-role prescriptions, we expected these effects to be evident among men, but not women. We test these hypotheses in a naturalistic study assessing retrospective behavioral reports and in a controlled laboratory experiment using behavioral coding to assess actual initiation behavior. Results were consistent with our hypotheses …