Although combining friendship and business in the same relationship can be beneficial, it can also create conflict. A source of this conflict is incompatible relational expectations. True friends are expected to be unmotivated by benefits that can be used beyond the relationship (e.g., money, status), whereas business partners are, by definition, at least partly motivated by these more “instrumental” concerns. Using a role theory framework and data collected from a survey of 685 direct-selling agents, this article reports evidence that a conflict between friendship and instrumentality can undermine some of the business outcomes that friendship might otherwise foster. It also suggests that this conflict is more severe for friendships that become business relationships than for business relationships that become friendships. Study conclusions do not suggest that friendship is entirely “bad” for business and, instead, propose that friendship’s influence can be both positive and negative.