ABSTRACTMobile instant messaging is experiencing immense growth, and using emoticons has become a prevalent and highly popular means of communication. The small digital images are ubiquitous, from smartphone applications to social media, and people delight in sending them. Drawing from construal level theory, the aim of this research is to examine the underlying mechanism that drives the usage of emoticons and its usage enjoyment. People with experience using mobile instant messaging were recruited to participate in an online survey, resulting in 202 usable questionnaires. The research model was tested empirically. Covariance-based structural equation modelling was used to analyze the data. The findings highlight that the determinants of individual’s emoticon usage are driven by a dual-route path. One is the self-concept route, where self-image congruity between emoticons and individuals drives psychological ownership, which in turn influences word of mouth (WOM) intention and perceived enjoyment of emoticon use. The other is the utility route, driven by emoticons’ familiarity and perceived synchronicity. The findings reveal the importance of emoticon usage through a contextual lens that shows that a dual-route path has a prominent impact upon these digital-based communication behaviours, which provides important managerial implications.