The prevalence of childhood obesity is almost 20% and affects 14.7 million youth. It is not a matter of if but when and how often sports medicine clinicians will care for patients with obesity. Considering the social, emotional, medical, and physical impact of obesity, we need a nuanced approach to communicate with patients and develop effective treatment plans to maintain or encourage physical activity. Neuromusculoskeletal impairments, physical complications, pain, biomechanical differences, and physical deconditioning act as potential barriers to treatment. This article introduces ways to pivot the conversation from musculoskeletal pain to a productive, well-received conversation about a holistic approach to weight management that also promotes physical activity and overall wellness in youth with obesity. Special attention is given to equipping clinicians with recommendations that incorporate the use of inclusive language, health behavior theories, and tenets of motivational interviewing to deliver equitable treatment regardless of body habitus.