Facebook is the most popular social networking site, with more than 500 million active members. With its ability to easily manage multi-user social networks synchronously, it provides a fertile foundation to promote e-mentoring among the current generation of technology- and Facebook-astute students. This study reviews Network of Practice (NoP) theories to provide insights to a mentoring structure that facilitates the sharing and exchange of profession-related knowledge. A Facebook application was developed to conduct an experiment that examined factors that affect the performance of the mentoring program based on a NoP. A class of college students, which used the application to connect to recent graduates and industry experts, allowed us to observe and analyze live mentoring activities. The authors' findings indicated that the mentor's gender appeared to impact the relationship that developed between mentors and protégés via Facebook, and that the students were indifferent about the years of experiences of their mentors.