Oral lesions can be a challenge to diagnose and treat. Talking, chewing, and swallowing cause friction within the mouth, making it difficult to determine the clinical appearance of the original lesion. Underlying health issues can also impact oral health so the patient health history, as well as the history and appearance of the oral lesions, is important to consider when diagnosing oral lesions. The patient presented here is a middle-aged man with oral lesions for 3 months, which severely impacted his life. This article allows the reader to identify a diagnosis based on information given, then discusses the differential diagnoses, and reveals the diagnosis and treatment plan.