What happens to the child who is off-putting to the people closest to him – when much of what he experiences from parents, peers and teachers tells him he is disappointing, annoying, or frustrating? At a young age, children can begin to identify with that disagreeable person reflected back to them. The author describes the psychodynamic, developmentally-informed play therapy of a strikingly disheartening six-year-old boy with ADHD, describing treatment that addressed his relational challenges and negative self-image along with the familiar triad of inattention, impulsivity, and hyperactivity. She reflects on her own clinical process throughout and describes how this informed the therapy.