This article describes the use of an eMentoring program by the Orphan Foundation of America, a nonprofit organization dedicated to helping young people move out of foster care and into adult life. The eMentoring program, which allows youth and their mentors to communicate via e-mail, helps foster youth prepare for work life by matching them with mentors based on their professional interests. The article includes highlights of the eMentoring process and a discussion of the benefits and risks of mentoring through e-mail. (GCP)