Whether teaching online or in a campus classroom, a significant part of the teaching life includes interacting with and responding to students. We respond to student comments and questions; their written work, exams, and presentations; their enthusiasm or lack thereof; and sometimes the personal joys and tragedies they share with us. We structure the course, the conversations, and the assignments and within this learning environment, we engage with a range of students who have various levels of motivation, preparation, insight, ability, positivity, negativity, and commitment.As we seek to understand and educate our students, and assess their work, we experience empathy, "a complex cognitive-affective skill that allows us to 'know' (resonate, feel, sense, cognitively grasp) another person' s experience" (Jordan 2010, 103). Empathy is part of the experience of teaching and is often present in our interactions and relationships with students as we (and they) seek to teach and learn the material, understand each other, and move through the course. Teaching and learning involve "a dance of responsiveness" (Jordan 2010, 4) and understanding this phenomenon helps us balance support and standards, role boundaries, and the power of connection in teaching and learning.In this chapter, we challenge tacit ideas about empathy that pervade both our larger culture and the teaching domain, and we suggest a more nuanced consideration of empathy in teaching and learning. We begin with an overview of Relational Cultural Theory (RCT), the theoretical foundation for this chapter and then review relevant teaching literature. Next, we explore the complexities of empathy in the context of teaching and learning. We consider why empathy is important in teaching, why it is sometimes difficult to feel empathy with certain students or in particular situations, and the pull we sometimes feel with students who are in crisis or even those who influence us more than we expect. Finally, we describe relevant stances and strategies for faculty including reflective approaches for use before and after specific interactions and in the midst of engagements with students. NEW DIRECTIONS FOR TEACHING AND LEARNING, no. 153, Spring 2018