Emoticons perform an important role as an enhancement to written communication, in areas such as Windows Live Messenger instant messaging, e-mails, mobile Short Message Services (SMS), and others. Emoticons are graphic images used in communications to indicate the feelings of people exchanging messages via mobile technology. In this research, the perceived usefulness of the emoticon in mobile phone text messages is verified with consumers using the five construct model of Huang. A K-means clustering technique for separating three groups based on levels of perceived usefulness of mobile emoticons is used with a structural equation model test using Smart PLS 2.0, and the bootstrap re-sampling procedure. We analyzed relationships among use of emoticons, enjoyment, interaction, information richness, and perceived usefulness. The results show there are relationships among use of emoticons, enjoyment, interaction, perceived usefulness, and information richness, however enjoyment of emoticons did not significantly affect the perceived usefulness of messages with emoticons alone. The results suggest emoticons have different affects on emotion in both mobile, and Messenger contexts. Our study did not consider more detailed media properties, and thus more studies are needed. Our research results contribute to mobile communication activation, provides companies with an understanding of key characteristics of consumers who use emoticons, and provides useful implications for improving management and marketing strategies.