We report a case of an immunocompetent 77-year-old Caucasian female presenting with bilateral herpes simplex keratitis masquerading as bilateral ulcerative blepharo-keratoconjunctivitis. Most cases of herpes simplex keratitis present unilaterally and uncommon occurrences of bilateral cases range from 1.3% to 10.9%. In literature, bilateral herpes simplex keratitis has been reported for patients with atopic disease, corticosteroid use, autoimmune diseases, and UV A light exposure. Our patient had none of these conditions, but she did suffer from type 2 diabetes mellitus that was well-controlled. She had no prior history of known herpes simplex disease and tested negative for COVID 19. To date, this is the third reported bilateral herpes simplex keratitis case and the second reported in an elderly patient with shared history of prostaglandin usage and presence of diabetes mellitus. Our rationale for reporting this case is that while it seems to be a rare presentation it could be establishing a pattern. The study explores the relationship between a prostaglandin and HSV activation that may allow viral entrance due to epithelial breakdown. Since our patient did not have any of the previously reported immunocompromised states that have been associated with bilateral herpes keratitis, this case may represent a new pattern for HSV infection. Our clinical methods indicate that close follow-up was crucial to identifying the patient's eye condition as a bilateral herpes simplex keratitis. Due to this potential pattern of disease, a revised management approach may benefit similar patients by selecting alternative treatments for glaucoma early in the disease presentation.