With the advent of apps like Facebook, WhatsApp, Twitter etc, messaging online has become very rampant. A very significant challenge of this is the comprehension effectiveness of these messages. The deciphering and comprehending of the messages sent on the above platforms are difficult since body language is removed from the context. Over the years, there has been an increase in the use of emoticons in messages. Emoticons and emoji have revolutionized digital communication by providing a way to convey emotions and add context to text-based messages. They have become an integral part of modern online conversations, enabling users to express themselves in creative and visual ways. These visual representations help in removing the ambiguity to an extent from the messages. In this paper, an attempt is made to study the usage of emoticons in WhatsApp messages and their role in comprehending them. Responses from 2571 respondents were collected and a multiple regression along with a path analysis was done to study the predictability of the type of emoticon and the usage frequency of emoticon on the message comprehension.