The purpose of this study is to investigate how self‐brand connection in an interactive multi‐actor single‐brand retail context can lead to consumers' willingness to pay premium through the sequential mediation of brand attitudes (intransigent and flexible) and brand love. Study 1 shows that self‐brand connection strengthens (weakens) consumers' intransigent (flexible) brand attitude, thereby increasing their brand love and willingness to pay price premium. Furthermore, consumers' high level of cynicism attenuates brand love and willingness to pay premium for consumers' displaying flexible brand attitudes. Study 2 shows that favorable other customer perceptions can mitigate the detrimental impact of high consumer cynicism on consumers' brand responses. In Study 3, we found that other customers' favorable behaviors (over similarity and/or appearance) can best mitigate the negative effects of consumer cynicism on brand love and willingness to pay premium. The research contributes by showing how varying degrees of consumers' self‐brand connection can develop willingness to pay premium through developing either intransigent (constructive route) or flexible (mitigating route) brand attitudes and brand love. For consumers harboring flexible brand attitudes accompanied with high cynicism, other customer perception serves as a conditioning tool, that alleviates their cynicism, and garners higher brand love as well as willingness to pay premium, and behavior dimension of other customer perception dominates in this quest.