As a means of psychological distancing, pretend play may facilitate emotion regulation. Up to now, however, the empirical evidence for a relation between these two is not consistent. The present study examines the impact of pretend play on reflective emotion regulation of expression with a disappointing gift task using the strategy of role-taking. Fifty-two children aged 3 to 6 years were motivated to deceive the experimenter volitionally by false smiling, regardless of whether they received an attractive gift, an unattractive gift, or no gift. Twenty-five of the children accomplished the task in the context of a pretend play where they were playfully guided to take on a role assumed to facilitate reflective emotion regulation of expression. The other 27 children received only a direct verbal instruction. As an indication of successful reflective emotion regulation of expression, twelve adult naïve observers judged children’s videotaped behavior according to the quality of emotion that the children seemed to experience. This impression analysis showed no impact of experimental variation and thus no facilitating effect of pretend play with a given task-convenient role. While happiness ratings in the pretend play group did not correlate to children’s quality of play, they positively correlated to children’s joy of playing.