A method, system, and computer program product for generating context-based tailored emoticons within a communication scenario are provided. The method receives detects an emotion of a user within a communication stream. A set of candidate emojis are generated. A set of emoticons are generated from the set of candidate emojis and a representation of the user. The set of emoticons are presented to the user in a user interface on a computing device associated with the user. The method incorporates a selected emoticon of the set of emoticons into the communication stream with the selected emoticon being selected by the user from the user interface.