Remarried stepfamilies are a sizable portion of American families; in a 2011 Pew Center survey, 42% of respondents reported at least one stepfamily member. Family clinicians and researchers suggest that stepparents’ ability to develop close bonds with stepchildren may be critical to the well‐being of couple and family relationships. Using actor‐partner interdependence models to analyze dyadic data from 291 heterosexual remarried stepfamily couples, we explored factors related to stepparents’ efforts to befriend their stepchildren. Specifically, we evaluated how remarried parents’ gatekeeping and stepparents’ perceptions of their attachment orientations were associated with their own and their spouse's perceptions of stepparents’ affinity‐seeking behaviors. Securely attached stepparents and stepparents with anxious attachment orientations engaged more frequently in affinity behaviors than did stepparents with avoidant attachment orientations; there was no difference between securely attached and anxious stepparents. Stepparents’ reports of parents’ restrictive gatekeeping were strongly and negatively associated with both stepparents’ and parents’ reports of stepparent affinity‐seeking (actor and partner effects). Parents’ reports of their own restrictive gatekeeping were also negatively (but more weakly) associated with parents’ reports of stepparent affinity‐seeking. Implications for families, clinicians, and relationship researchers and theorists are discussed.