Research on the relationship between military service and eating pathology has yielded mixed findings. Among those of military backgrounds, anorexia nervosa typically presents with co-occurring disorders that complicate diagnosis and treatment. The purpose of this paper is to present a case report of a retired Navy midshipman. The patient sought treatment for obsessive compulsive disorder (OCD), but his assessment revealed the primary pathology to be anorexia nervosa. This case illustrates ways in which military life may contribute to eating pathology and the complex overlap and differential diagnosis of anorexia nervosa and OCD.