Although widespread belief holds that salespeople can leverage their personal relationships with prospective customers to gain business, previous research has not investigated the implications of friendships between salespeople and customers for customers’ postpurchase satisfaction and fairness judgment. Findings from two experiments show that friendships benefit salespeople only when the outcome of the transaction is unfavorable. Specifically, when salespeople and customers are close friends rather than acquaintances, the customers perceive an unfavorable outcome as relatively more fair and satisfactory, but such an effect does not occur when the outcome of the transaction is favorable. This paper also shows that customers’ perceived fairness mediates the interaction effect between friendship and the favorability of transaction outcome on customer satisfaction. In summary, this paper advances the understanding of the implications of salesperson–customer friendships for customers’ postpurchase evaluations.