This study sought to explore and better understand the importance and impact of labels in our secondary schools and society for students and educators at a small Northeast high school and how they in turn view themselves and others as a result of their interactions and experiences with labeling. What made this study important and different from previous studies was that no one particular label was investigated and that multiple labels were examined simultaneously. The twelve individuals involved in the study were a mix of staff and students from a variety of backgrounds who had both overlapping and unique experiences with labels and labeling. An interpretive phenomenological analysis (IPA) served as the methodology to better understand the intricacies and entanglements that labels have caused for the participants during their time in high school; both personally and professionally. The firsthand narratives of the participants provided detailed accounts for inductive analysis at the school under investigation. The study revealed that people's experiences with labels, while individual and inimitable, shared some commonalities in terms of impact. The four themes of normalization, liminality of labels, identity confusion and feelings of conflict were present across all of the conducted interviews to varying extents. Specifically, although people were familiar with the use of labels and labeling in schools they were far from comfortable with it. This discomfiture, if not vexation, was further confounded by the fact that the meanings and appropriateness of labels are constantly changing and, as such, ultimately contribute to confusion during the development of identity during adolescence and conflict that shapes their perceptions well into adulthood as well.