This article is a response to calls for more research on empathy and service-learning and is driven by the author team's deep interest in how empathy, gender, and personal connections shape students' service-learning experiences. To understand this issue, they have focused on an often-overlooked moment in the student's service-learning experience: choosing a site in which to work. The article begins by providing some background on the literature about the connections between gender and empathy in service-learning classes and about service-learning site selection. Then, through the responses of survey participants and the voices of two interview participants, the authors explore some factors that influence students' site selections and consider what role(s) empathy might play in those selections as well as in students' actual service experiences. The article concludes with some suggestions of valuable practices that feminist teachers of service-learning courses might use to promote a model of civic engagement that honors students', instructors', and community partners' feelings and experiences and encourages each of these groups to make productive and socially connected choices.