For the initiated, college may be remembered as a care-free and playful time. However, for contemporary college students the transition to college is challenging with only 1 in 3 returning for their second year of study, and the challenges are even greater for first-generation and low-income students. The interactive digital platform of the current study invited low-income first-year students to write about and reflect upon their transition to college. It was through the higher order cognitive process of writing, which involved deciding which words, symbols, and punctuation to use to express a particular thought to a particular audience, that the students made-sense of their experiences. Our analyses detail how students integrated new approaches for communicating their thoughts in writing and how these techniques changed over time. We show how first-year students used the affordances of the keyboard and an interactive blog to create a reflective and supportive digital writing style somewhere between the formality of the college essay and the freewheeling social media post. The emerging playful style was marked by the introduction of computer-mediated communication (CMC) cues typical of social media platforms like Twitter and Facebook, including emoticons and emojis, hashtags, repeated capital letters, repeated punctuation, and abbreviations such as lol, to the college course context. A path analysis of 209 blog posts and 161 comments over four time points, coupled with a qualitative case study showed that students developed their use of CMC cues first on the social level through comments and later on the individual level in their posts. Our analyses show how students integrated CMC cues to communicate humor and critique as they created a new genre of college writing. The social support and the CMC cues were concretely relevant to the students' development of knowledge and practice of what it meant to write in college and what it meant to become a college student.