Findings suggest that mentors and youth approach the mentoring relationship with expectations that, if not met or acknowledged and appropriately addressed, can interfere with the mentoring process. In addition, the findings suggest that in some cases mentors may state that they are ending their relationship due to an unanticipated life event or the sense that they are “too busy” when they are experiencing some type of difficulty in the match. The narratives of some participants indicate that mentors may not readily identify the difficulties or disappointments they are experiencing and life events can become easy excuses for ending an already troubled relationship. The results clearly show the importance of continued examination of mentoring relationship failures. Greater attention to the range of participants’ experiences in mentoring relationships would offer better guidance for ways to improve youth mentoring program practices. The appeal of youth mentoring programs is great and the enthusiasm for youth mentoring is not without some cause. However, there has been little to no discussion of mentoring relationships that do not make it. This study details some of the negative experiences encountered by a group of mentors and youth and points to roles programs may be able to play in potentially preventing some relationship failures. A total of 31 male and female participants were recruited from 2 Big Brothers Big Sisters of America community-based mentoring programs in the Northeast. Table, references