Emoticons are graphic signs used to enrich and support computer-mediated verbal interactions (CMC). The most famous type of emoticon is represented by the icons of facial expressions: :-), :-(, ;-), etc., that most frequently occur in instant messagging and e-mails. Falling within the scope of the pragmatics of CMC, this paper examines the extent to which the aim of a conversation and the conflicting or cooperative nature of a conversation influence the frequency of using emoticons (with either a positive or a negative value) on WhatsApp. The data collected from a behavioural experiment support some preliminary conclusions: WhatsApp users tend to use emoticons most frequently in positive and cooperative contexts as well as in socio-emotional verbal exchanges. Even though emoticons are used less frequently during conversations that are geared towards the accomplishment of a given goal, it is in such contexts that the emoticons with a positive value (e.g., :-)) occur most frequently.