One of the hallmarks of emotional intelligence is the ability to regulate emotions. Research suggests that cognitive reappraisal - a technique that involves reinterpreting the meaning of a thought or situation - can down-regulate negative emotions, without incurring significant psychological or physiological costs. Habitual use of this strategy is also linked to many key indices of physical and emotional health. Unfortunately, this technique is not always easy to apply. Thinking flexibly about stressful thoughts and situations requires creativity and poise, faculties that often elude us when we need them the most. In this paper, we propose an assistive technology that coordinates collective intelligence on demand, to help individuals reappraise stressful thoughts and situations. In two experiments, we assess key features of our design and we demonstrate the feasibility of crowdsourcing empathetic reappraisals with on demand workforces, such as Amazon's Mechanical Turk.