The aims of this mixed-method pilot study were to determine the feasibility, acceptability, and preliminary psychosocial outcomes of “Making Friends with Yourself: A Mindful Self-compassion Program for Teens” (MFY), an adaptation of the adult Mindful Self-compassion program. Thirty-four students age 14–17 were enrolled in this waitlist-controlled crossover study. Participants were randomized to either the waitlist or intervention group and administered online surveys at baseline, after the first cohort participated in the intervention, and after the waitlist crossovers participated in the intervention. Attendance and retention data were collected to determine feasibility, and audiorecordings of the 6-week class were analyzed to determine acceptability of the program. Findings indicated that MFY is a feasible and acceptable program for adolescents. Compared with the waitlist control, the intervention group had significantly greater self-compassion and life satisfaction and significantly lower depression than the waitlist control, with trends for greater mindfulness, greater social connectedness, and lower anxiety. When waitlist crossover results were combined with that of the first intervention group, findings indicated significantly greater mindfulness and self-compassion, and significantly less anxiety, depression, perceived stress, and negative affect post-intervention. Additionally, regression results demonstrated that self-compassion and mindfulness predicted decreases in anxiety, depression, perceived stress, and increases in life satisfaction post-intervention. MFY shows promise as a program to increase psychosocial well-being in adolescents through increasing mindfulness and self-compassion. Further testing is needed to substantiate the findings.