Mobile instant messaging is the communication technology revolution that is changing the way people communicate. The adoption rate is surging and the massive growth is experienced worldwide. Prior studies in instant messaging has been primarily concerned with its task relevant or functional aspects, with less attention on social interaction aspects. Drawing from media richness theory, present research highlights that social interaction factors can be facilitated by the enriched communication channel to build closer interpersonal social relationship. Specifically, the findings illustrate that combined effect of text messaging and the use of emoticon, builds information richness which leads to perceived playfulness in mobile instant messaging. Furthermore, the perceived playfulness fostered in the instant messaging process, plays a driving role in facilitating social connectedness, identity expressiveness between the users and the advocacy of mobile instant messaging usage.