This study examined the interaction between college students' attachment orientation and mentors' relational style in the prediction of students' behaviors and perceptions in academic mentoring and of their subsequent academic achievement. Ninety college students were administered the Adult Attachment Interview and their professors-mentors completed the Attachment Style Questionnaire. Students displayed more adaptive behaviors and perceptions in mentoring and earned higher grades when their attachment orientation was in contrast to their mentor's relational style. Implications for the practice of academic mentoring in college are discussed.