Conducting scholarship and teaching about socially constructed aspects of identity (e.g., race, ethnicity, sexual orientation, age, and class) often presents challenges to communication scholars. Within this article, we discuss some of those challenges by disclosing aspects of our lived experiences as “outsiders within” the academy. Through analyzing e‐mail messages that we exchanged with one another, we explore complexities of our emotions (and ensuing tears) as we experience both enchantment and disenchantment with how members of the academy deal with difference matters. We rely upon feminist standpoint epistemology as our theoretical framework, and we specify dialogic theory and ontology as a promising means by which we can transform the academy.