Syphilis is a sexually transmitted infection caused by Treponema pallidum. It progresses through three clinical stages and shows various oral symptoms, mainly during the secondary stage. The disease can resemble other common oral mucosal conditions, such as infections with nonspecific pharyngitis, tonsillitis and laryngitis, as well as neoplastic and immune-mediated ulcers. This report discusses a heterosexual couple with rare manifestations of primary and secondary syphilis involving oropharyngeal lesions and an extragenital chancre, highlighting the diagnostic challenge and the importance of clinical awareness for early detection and treatment.