Factitial cheilitis is a rare diagnosis of exclusion that occurs most frequently in young women with a history of anxiety disorders and recent psychosocial stressors. It presents as continuous keratinaceous build-up, crusting, and desquamation of the lips, consistent with exfoliative cheilitis. Affected areas can progress to superinfection with Staphylococcus aureus or Candida albicans. We report a case of a 23-year-old woman who presented with diffuse hyperkeratosis of the upper and lower lips that was initially suspected to be allergic or irritant contact dermatitis based on clinical examination. Clinical and histologic correlation of two separate biopsies plus a negative infectious workup led to the consideration of a factitial etiology. Through open and direct communication between the patient and the provider, the appropriate diagnosis was discerned. Referral for the psychiatric symptoms as well as management of the same resulted in complete resolution of her lip findings. This case highlights the importance of considering factitial cheilitis as the etiology of exfoliative cheilitis, especially in the presence of concomitant psychiatric disorders.