This study describes the history of online icons that originated in the West, as well as changes in expressions that accompany multiple writing behaviors in cyberspace. After a period of using a certain medium, online users accumulate specific use knowledge and skills to facilitate online communication. The next discussion focused on the creation of graphic symbols and lexicons used to represent emotions in computer-mediated communication culture. Similar or different symbols representing the same emotions but categorized according to a certain culture were then identified. An “emoticon,” a portmanteau of an emotion and an icon, is textual expression representing the face of a writer's mood to alert a recipient or to temper a statement. From social and cultural perspectives, the embedded meaning and connotation of lexes and emoticons were analyzed by collecting user-generated Web content. This research determined that, in assessing emotions communicated by using computer-mediated content, some basic emotions and fundamental facial expressions did not necessarily correspond to the emoticons. In addition, most of the emotion icons found in this study were for the state of emotion, not emotion per se. Although multiple lexicons and emoticons may be exhibited, emotion lexes and affection icons are highly contextual and culturally specific. The potential effects of emotion icons are discussed and the implications and limitations for future study are also indicated.