Fractures of the proximal fifth metatarsal are among the most common fractures of the foot. History, physical examination, and subsequent radiographic work-up can help with the diagnosis of such a fracture. Many fractures of the proximal fifth metatarsal can have an associated prodrome, thereby establishing a level of chronicity to the problem. Identification of the location of the fracture plane within the proximal fifth metatarsal can have prognostic implications in regards to fracture union rate and guide treatment options, due to the particular vascular anatomy of the region. Additional findings on physical exam, such as heel varus, can also impact prognosis and treatment options. Treatments can range from nonoperative to operative modalities, and time to weightbearing can vary. Within the realm of operative treatment, identification of certain parameters can aid in successful reduction and fixation of the fracture and thus impact healing. Careful consideration of the patient's particular constellation of social and professional needs, clinical and radiographic parameters, and acceptance of different options can help guide treatment recommendations in the individual patient.