ABSTRACTPoint‐of‐sale anthropomorphism—attributing human characteristics to nonhuman entities—has been shown to increase evaluations of food that deviates in shape or form from consumer expectations (“imperfect food”). However, while previous research has included the use of primary emotions to manipulate anthropomorphism, it is unclear whether depicting imperfect produce with happy or sad emotional expressions is more effective in boosting choice of such produce. This research addresses this gap and additionally examines a novel type of imperfection: when produce is torn off the bunch it normally comes in. A field study conducted at a large food retailer in Germany revealed that sales of “single” bananas significantly increased when they were anthropomorphized with sad emotions compared to when they were anthropomorphized with happy emotions or not anthropomorphized. Across three preregistered online experiments, this research corroborates the effectiveness of sad emotional expressions in boosting purchase intentions, establishes compassion as the underlying process, generalizes this effect to other produce (i.e., tomatoes), and shows that a price discount eliminates this effect. The findings of this research are particularly relevant for food retailers aiming to increase purchases, and thus reduce waste, of fresh produce that has become a loose “single.”