A healthy 53-year-old man presented for sexually transmitted infection (STI) screening after being informed by the health department that he had sexual intercourse with a male partner who was recently diagnosed with and treated for syphilis. He acknowledged having unprotected sex with male partners, reported no history of syphilis or Human Immunodeficiency Virus (HIV), and denied any penile lesions, discharge, or rash. Rapid plasma reagin (RPR) and Treponema pallidum particle agglutination (TPPA) assays were ordered, but the results were not reviewed. No futher testing or physical examination occurred; he was treated with one intramuscular dose of penicillin and no further follow-up was indicated. Two years later, the patient presented to his primary care provider (PCP) with symptoms of neurosyphilis. He was treated with 14 days of intravenous penicillin but had both an inflammatory reaction to the treatment and complications of tertiary syphilis. The commentary discusses the importance of conducting a complete physical examination and gathering a complete patient history, and describes the historical and cultural context of stigma that lesbian, gay, bisexual, and transgender, queer and/or questioning, intersex and asexual and/or ally (LGBTQIA) populations face.