Healthy romantic relationships are positively associated with physical and mental health outcomes, and past research has shown that traditional masculinity negatively impacts relationship satisfaction. The current study examined the effects of men's discrepancies between their self-ratings and perceptions of their peers' on autonomous and pressured motivations to act agentically on relationship outcomes for both partners in a heterosexual relationship. In addition, men's investment in gender ideals was measured as a potential moderator and men's self-esteem as a potential mediator. Specifically, it was predicted that men's self-esteem would mediate the association between the investment-by-discrepancies (autonomous and pressured) interactions and relationship satisfaction reported by both partners. Results of polynomial regressions on 183 romantic relationship dyads did not support predictions. Limitations presented include scale validity, the correlational design of the study, and the conceptualization of pressured and autonomous motivations as opposites of each other. Future directions included exploring the various forms of men's agentic extrinsic motivations and how they associate with relationship outcomes; and the utilization of real-time relationship behaviors observed during an interaction between romantic relationship partners.