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Thrombophlebitis of the superficial dorsal penile vein is an infrequently reported condition that presents with pain and induration at the base of the penis. Known clinically as the penile variant of Mondor's disease (PVMD), this rare pathology can elicit fear and embarrassment in patients, making it difficult for them to seek medical care. PVMD is also frustrating to clinicians, as its etiology can be varied, typical laboratory abnormalities are often absent, its presentation can be imitated by other diagnoses, and a consensus on treatment has not yet been reached. As depicted in this case report, this challenging diagnosis requires the collaboration of primary care physicians and urologists to optimize patient care.