A qualitative analysis of 51 matches between volunteer mentors and pregnant adolescents is discussed in terms of problems that occurred and reasons relating to early termination of the match. In each of three stages of the relationship, different issues related to the behavior and interpersonal process between members of the match created problems. In stage one, the mentors had difficulty establishing the match when there was avoidance, distrust, and testing behavior on the part of the mentee. Fear of intimacy and rejection seemed to underlie these relationship difficulties. In stage two, which encompassed the birth of the adolescent's child, conflict occurred when mentees' demands overwhelmed the mentors. In the third stage, difficulties discussing termination or continuation of the relationship led to disengagement and less frequent contact. Recommendations are provided to help mentors and mentees navigate the problems in each of these stages.