Background: Adolescence is a challenging time for families, which is intensified when managing a chronic health condition. In adolescents with severe obesity, little is known about how adolescent/mother dyads approach management. Our study aims to (1) explore similarities/differences in adolescent/mother dyads' perceptions of weight management behaviors and (2) describe their experiences with successes and challenges related to weight management. Methods: This was a qualitative descriptive analysis of interviews from 21 adolescent/mother dyads. Conventional content analysis was used to identify themes characterizing dyads' weight management efforts. Results: Two patterns of perceptions were identified across the dyads specific to weight management behaviors: collaborative (dyads agreed) and conflicting (dyads disagreed). Weight management themes with collaborative perceptions were food preferences; food and emotion; the adolescent is active; exercise is not enjoyable; the family is active together; and stopping medications. Weight management themes with conflicting perceptions were responsibility for initiating and maintaining exercise, motivation and willingness to exercise, and responsibility for medications. Dyads had collaborative pattern responses on perceptions of success and challenges. Themes related to successes were weight loss and supportive relationships. Themes related to challenges were inconsistent daily routines and schedules, and unsupportive relationships. Conclusions: Dyads responded with collaborative or conflicting perceptions to weight management behaviors and with collaborative responses to success and challenges. Sustaining healthy habits was difficult from the perspectives of dyads. For youth with severe obesity, providing care that recognizes and addressees issues youth and their families experience may require improved and innovative interventions.