Until recently, despite the deleterious the health consequences of their obesity, intentional weight loss by older adults usually was not recommended. Factors such as maladaptive metabolic changes and declines in physiologic function predispose this population to sarcopenic obesity, frailty, and impaired mobility, while accumulation of chronic comorbidities often results in polypharmacy. These considerations and more complicate both the decision to pursue weight loss and the safest method of doing so. Currently, specific guidelines for managing weight loss in older adults with obesity are widely lacking. We present a case from our Family Medicine practice of an older woman with obesity struggling with weight management. We present our recommendations for safely navigating the weight loss she desires using an evidence-based approach that incorporates a medically supervised calorie restricted diet, improved diet quality, and healthy physical activity recommendations that include resistance exercise.