WhatsApp messages can be such a rich source for creative and spontaneous language geared toward more individual expression. WhatsApping provides us with a unique view into language and is an interesting prototype for thinking about language use, the various functions of this variety and how it is used to render different kinds of meanings. This study aims to explore the linguistic features of text messaging's communicative intent, content and context. Selected samples of messages were drawn from a high school student population in Canada who provided a corpus of 100 different texts already sent and/or received for personal, educational and professional purposes. The collected data were analyzed using Biber and Conrad's qualitative approach to register, genre, and style analysis. The result is that people use clipped sentences in a free flow of casual speech and slang. While certain abbreviations have come into such common use, to the point of becoming standard, a wide array of individualistic variance in terms of style and language usage has emerged. It is concluded that avid texters, while appearing to greatly deviate from more traditional, standard written English, are a rich source for studying creative and spontaneous language adaptation of register, genre and text according to context and text users.