Research in general education suggests that relationship-building is at the core of quality learning experiences. Yet relationship-building has not received the attention, it deserves from researchers in the field of TESOL where teacher-student relationships of various types are a central component in successful teaching and learning. This article examines the perspectives of three experienced English as a Second Language teachers on teacher-student relationships and the nature and importance of personal and emotional investment in relationship-building, elicited during group discussions in a teacher reflection group in Canada. Results indicate that the entertainer-audience pedagogical relationship was important for all three teachers, but also raised questions for them which they had to address. In addition, setting boundaries for teacher-student relationships and the issue of student responsibility were reflected on by all three teachers.