Major parts of today’s economy are based on service jobs that include the deliberate regulation of emotions during customer contact. Organizations aim at creating pleasant customer interactions in order to provoke desirable reactions (e.g., higher turnover, less cancellations and complaints) that may ensure and increase commercial success. At the same time, employees are often challenged with stressful job demands that may impair their subjective well-being and their actual capability to shape customer relations in a positive way. Therefore, the aim of the present study is to investigate the relationship between job demands and the quality of customer contact. Specifically, we investigate how time pressure is related to the adoption of positive and negative humor in interactions with retail customers, and whether the emotion work strategies of deep and surface acting mediate these relationships.