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Teacher-student relationships are vital for academic and social development of students, for teachers’ professional and personal development, and for having a supportive learning environment. In the digital age, these relationships can extend beyond bricks and mortar and beyond school hours. Specifically, these relationships are extended today while teachers and students communicate via social networking sites (SNS). This paper characterizes differences between teachers (N= 160) and students (N= 587) who are willing to connect with their students/teachers via Facebook and those who do not wish to connect. The quantitative research reported here within is based on data collection of personal characteristics, attitudes towards Facebook, and perceptions of teacher-student relationship. Findings suggest differences in characteristics of the two groups (willing to connect vs. not willing to connect) within both populations (teachers and students). Also, in both populations, those who were willing to connect, compared to those who were not willing to connect, present more positive attitudes towards using Facebook for teaching/learning and are more opposed to a banning policy of student-teacher SNS-based communication. We also found that students who were willing to connect showed a greater degree of closeness with their teachers compared to those who were not willing to connect. This study may assist policymakers when setting up regulations regarding teacher-student communication via social networking sites.