Emoticons are graphic signs, such as :-)(smiley face), that often accompany textual computer-mediated communication (Dresner & Herring, 2010). Emoticons are thought to be used to convey emotion (Derks et al, 2007; Wolf, 2000). Specifically, it is believed that emoticons supplement electronic communication with non-verbal cues, such as those often seen in face-to-face communication (Lo, 2008). We collected text messages from participants who also rated the messages across a number of emotional dimensions. We asked a separate group to rate the same messages on the same dimensions. By comparing when a particular emoticon was used, the emotional qualities of the message as rated by both the sender and reviewer, we aim to investigate which emoticon is likely to be included in text messages according to emotional intent, and whether this emotional intent will likely be understood.