This paper reports results from a longitudinal field experiment examining the evolution of relationships between consumers and an on-line photography brand in response to brand personality and transgression manipulations. Development patterns differed significantly for the two personalities, whereby relationships with sincere brands deepened over time in line with friendship templates, and relationships with exciting brands evinced a trajectory characteristic of short-lived flings. However, these patterns held only when the relationship proceeded without a brand transgression. Relationships with sincere brands suffered dramatically and irrevocably in the wake of transgressions but, surprisingly, showed signs of reinvigoration for exciting brands. Character inferences concerning the quality of the brand as a relationship partner mediated the results. Findings suggest a dynamic construal of brand personality, greater attention to interrupt events including transgressions, and consideration of the relationship contracts formed at the hands of different brands.