In a case involving an older teen who was in and out of the hospital, urgent care and the physician’s office, not a single healthcare worker asked how the teen was feeling and in some cases the parent in the room had to help the physician ask the right questions. For example, the doctor thought it was odd that this patient was waking up in the middle of the night with severe headaches. He was right to question this but failed to ask if the teen ‘usually’ woke up and failed to ask any lifestyle behaviors. The case highlights difficulties in making healthcare decisions in the acute setting and the challenges and responsibilities families have in managing behaviors, not overreacting to every symptom, and being more engaged with physicians and physician assistants who often default to a script for a medicine.