In this dissertation, I examine the mediating role of emotion during lived interactions between students and teachers at an urban charter high school. While the importance of student-teacher connectivity for positive school engagement has been well documented, research that attempts to describe the mechanism of that link is scarce. This qualitative study, which is also practitioner-based research, investigates how emotions facilitate and impede intersubjectivity during classroom interactions between students and teachers across one semester of a school year. I explored both student and teacher perspectives by interviewing and observing 17 student-teacher dyads as they connected (or did not connect) through a shared field of affective experience, called "emotional intersubjectivity" (Denzin, 2007). My findings suggest that urban teachers exert persistent self-regulatory efforts, known as "emotional labor" (Hochschild, 1983), as they pursue students towards the institutional goal of academic achievement. Inductive coding indicates that there are five general domains of emotional labor that occur in pursuit of student connection. I describe each domain in detail. It also reveals several affective-behavioral patterns which, when enacted by urban teachers, tend to facilitate "practical intersubjectivity" (Biesta, 1994), thus paving the way for knowledge co-construction. These regulatory patterns, if adapted to actionable skill sets, could positively impact the content of urban teacher education programs. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]