The present study investigates the role of proximity in shaping static and dynamic social income comparisons and their association with self-assessed health, a subjective health-related dimension of individual well-being. Using the Spanish Survey of Household Finances (2002–2017), the study examines how individuals compare their income trajectories with those of their peers, considering varying degrees of proximity. The findings reveal that health-related well-being is negatively associated with static comparisons only in the case of a significant income gap with richer individuals. However, when dynamic comparisons are introduced, we observe a positive association with self-assessed health when comparing to individuals who previously earned more but now earn less, as long as they drop at a certain distance. Consequently, no effect is observed when comparing with individuals in closer proximity, and effects emerge when the degree of proximity is low.