During the same time period social media increased in popularity and regularity of use, mental health challenges for first-year college students reached an unprecedented high. Both of these variables, individually and together, connect emotion and thought to writing and the first-year student’s daily understandings. During these transformative decades, composition studies experienced a pedagogical shift. By drawing connections among pedagogies, this thesis argues for the re-addressing of expressive elements within critical pedagogy as a means for more effectively engaging socially tethered students who might be experiencing (directly or indirectly) anxiety and/or depression. Critical expressive pedagogy builds on emerging theories to help students better navigate the blurring line between private and public audiences for healthy processing and disclosing of written words. To best demonstrate these complex theories, a webtext synthesizing the variables is presented.