People actively use emojis as an equivalent tool for the absence of nonverbal cues in online communication. Prior studies showed that emojis or emoticons may not merely influence receivers’ emotions but also the formation of impression. However, how emoji usage influences receivers’ behavior in the organization is still unknown. Drawing on politeness theory, the present study proposes that the usage of smiley emojis in the help request context may positively influence receivers’ helping behaviors via pleasure; trait cynicism of receivers which influences the interpretation of message is likely to moderated such the indirect effect. By adopting a mixed research design with an interview (N = 11), an experiment (N = 120), and a field survey (N = 214), we found that when receivers’ trait cynicism is lower, the indirect effect of smiley emoji usage on receivers’ helping behaviors via pleasure is stronger. Our study suggests smiley emoji usage as a social lubricant in organizational communication.