["Psychology &Marketing, EarlyView. ", "\nABSTRACT\nMarketing self‐improvement products as gifts is challenging for brands. Recipients often feel insulted and may spread negative word‐of‐mouth, prompting the need for marketing interventions such as financial incentives. Yet, the psychological mechanisms—and thus the marketing strategies—that drive people to gift such products remain poorly understood. Drawing on the evolutionary psychology perspective of friendship and the results of five studies, we demonstrate that downward financial comparison increases the likelihood of gifting self‐improvement products. This pathway is mediated by compassion and moderated by autonomy‐oriented help‐seeking and marketing communications that evoke a self‐directive brand concept. Our findings contribute to the literature on self‐improvement gifting by identifying the factors that motivate this behavior. Beyond its marketing implications, the study contributes to broader societal debates on economic connectedness and inequality, suggesting that decisions by wealthier individuals to help their less wealthy friends are shaped by both interpersonal comparisons and moral and emotional processes.\n"]