There is a need for mental health interventions for youth in the United States. Youth mentoring programs have proven to be successful in helping in a variety of aspects. The purpose of this phenomenological study was to gain insight into the lived experiences of participants in a therapeutic youth mentoring program. In addition to being paired 1:1 with a mentor, all of the youth had access to individual counseling with counselors-in-training throughout the program. The participants in this study were 14 youth, ages 11–15, who were considered “at-promise youth” if they were not reaching their full potential in the school setting and might be vulnerable to school dropout, substance use/misuse, and/or criminal behavior. All participants were interviewed at the beginning and end of a 12-week therapeutic mentoring program. Five themes emerged from the data: life stressors, self-awareness, trusting others, adaptability and resiliency, and hope for the future. Researchers observed an increase in participants’ self-esteem, self-efficacy, and problem-solving and coping skills. Implications for counselors, particularly those interested in adding a therapeutic component to traditional mentoring programs, are discussed along with suggestions for future research.