Surrogates who must make medical decisions for other people—most often, loved ones—face difficult challenges not acknowledged in current models of medical decision making. Furthermore, medical decisions are typically not a single event, but an ongoing event that evolves over time. This chapter presents a broader conceptualization of medical decision making, highlighting that (1) surrogate decision makers often face multiple problems, not a single clear problem; (2) the path to the decision maker’s desired goal is often unclear and often constrained by past decisions; (3) the social relationships between the surrogate and the patient (parent, adult child, spouse) influence the decision making as surrogates try to fulfill their role as a good parent, good son/daughter, or good spouse; and (4) surrogate decision makers often judge themselves negatively in ways that influence their decisions and the outcome. Clinicians who recognize these complex influences on surrogate decision making may be better able to support surrogates through this difficult process.