Objectives: Guided by interpersonal theory, this study examined the links between everyday perceptions of interpersonal dynamics, trait-level interpersonal styles, and time-varying social contexts (i.e., with spouses, family, non-family) as they unfold in older people’s everyday life. Method: A sample of 78 late-middle-aged and older adults completed 2,739 reports of their social interactions over a one-week period (average 5.02 per day, SD = 2.95). For each report, participants recorded their perceptions of their own agentic and communal behavior, as well as that of their partner. Results: Results from multilevel modeling revealed that the complementarity in agentic behaviors was stronger when people were interacting with spouses and family members, whereas such contextual differences were not found to influence the degree of communal complementarity. Individuals with higher level trait agency tended to view their partner as more agentic across interactions with different social partners. Individuals with higher level trait communion tended to view their partner as more communal during interactions; this tendency was more pronounced when interacting with non-family members. Conclusions: The differing degrees of perceived complementarity along the dimensions of agency and communion should be understood through varying social contexts. Participants’ trait interpersonal styles tended to affect how they viewed the agentic and communal behaviors of others.