Choices are often difficult to make by patients with Alzheimer Dementia. They often become acutely confused when faced with too many options because they are not able to retain in their working memory enough information about the various individual choices available. In this case study, we describe how an essentially simple benign task (choosing a dress to wear) can rapidly escalate and result in a catastrophic outcome. We examine what went wrong in the patient/caregiver interaction and how that potentially catastrophic situation could have been avoided or defused.