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Syphilis is often referred to as "the great masquerader," as it may present with a wide array of clinical symptoms and may mimic a variety of other diseases making diagnosis challenging. We report the case of a young, married woman who presented with a one-month history of significant hair loss, unintentional weight loss, blurred vision, and intermittent headaches. In addition, she endorsed positional dizziness and intermittent arthralgias. Physical exam was only remarkable for a non-scarring alopecia over the frontal marginal ha