Homework assignments in psychoanalysis are contentious; some believe they contradict psychoanalytic principles, while others argue they enhance coping skills. We propose that homework can be a legitimate aspect of relational psychoanalysis when used in a way that is attuned to the patient’s experience and that homework may be an important component of treating personality disorders. We present the case of a man diagnosed with narcissistic personality disorder to illustrate this: the patient, wrestling with social relations and control dynamics within therapy, was assigned homework aimed at curbing his compulsive caregiving and exploring its underlying motives. This exercise led him to understand his actions stemmed from avoidance of exposing his vulnerabilities. Subsequently, he was able to engage with relationships from diverse perspectives and discover new meanings. We advocate that homework tasks can be successfully incorporated into the relational psychoanalytic approach, fostering self-reflection and facilitating transformative change in patients with personality disorders.