Attachment to the bad object has remained a durable, undertheorized clinical problem. With an extended clinical example, the experience of limit, in both patient and analyst, is examined as part of a dense undercurrent in the relationship, including transference, that gives rise to shifts in understanding the attachment to an unsatisfying internal object. Importantly, the patient's and the analyst's experiences of limit are “in play” during the process of changes in the patient's attachment to the bad object. The relation of patient and analyst to the patient's internal objects, including bad and unsatisfying objects, is where play itself begins. Limit itself is constitutive of play. The analyst's attempt to analyze his own thoughts and experience regarding limits in maintaining an empathic connection to the patient's psychic reality influences the patient's capacity to take in a new part of his or her experience.