Meeting the diverse needs of young people who are coping with such problems as delinquent behaviors or poor academic performance is an urgent issue today. This paper aims to demonstrate the benefits of introducing intergenerational mentoring activities into educational programs for supporting "at risk" adolescents by highlighting some innovative and effective methods. Among various types of mentoring activities, this paper will focus on ones in which older adults take on the role of mentors. The significance of mentoring activities in which older adults give emotional support to at risk adolescents has been recognized since the late 1980s in the United States. An important component of this type of "intergenerational mentoring" initiative involves establishing a sense of mutual trust between the older adult mentors and the at risk youth mentees. This paper consists of the following parts. Firstly, the author will describe the rationale and some of the societal factors that are contributing to the emergence of the mentoring activities for at risk adolescents in contemporary society. Secondly, the author will describe key characteristics of intergenerational mentoring activities designed to support at risk adolescents. The primary focus will be on lessons learned from an intergenerational mentoring program called "Across Ages" which is operated by Temple University's Center for Intergenerational Learning. In analyzing this model program, the author will focus on challenging issues related to how the mentor role is constructed and how the mentors function in the context of program goals to produce benefits for the participants. Finally, in concluding this paper, the author will point out that such intergenerational mentoring endeavors not only expand informal helping resources for at risk adolescents but also help in establishing a circulative mentoring process that has implications for the enrichment of the lives of people of all ages in the community. (Contains 14 notes.)