This paper presents a new conceptual model that generates predictions about breastfeeding decisions and identifies interactions that affect outcomes. We offer a contextual approach to infant feeding that models multi-directional influences by expanding on the evolutionary parent–offspring conflict and situation-specific breastfeeding theories. The main hypothesis generated from our framework suggests that simultaneously addressing breastfeeding costs and benefits, in relation to how they are interpreted by mothers, will be most effective. Our approach focuses on contributors to the attitudes and commitment underlying breastfeeding outcomes, beginning in the prenatal period. We conclude that some maternal–offspring conflict is inherent with the dynamic infant feeding relationship. Guidance that anticipates and addresses family trade-offs over time can be incorporated into breastfeeding support for families.