Sexually transmitted diseases/infections (STDs/STIs) are one of major public health concern, and syphilis in today’s era is not an uncommon diagnosis. The rising trend of syphilis cases can be attributed to changes in sexual practices such as individuals being engaged in oro-genital or anogenital sex, having multiple sexual partners, increase in men having sex with men, HIV co-infection, and drug abuse. Syphilis mimics many other diseases, and diagnosis can be delayed if the clinician is not aware of varied presentations. Often, unusual mucocutaneous manifestations have fascinated dermatologists, leading to diagnostic difficulties. In today’s era, cases of secondary and latent syphilis are being more commonly encountered than those of primary syphilis. Herein, we emphasize on varied mucocutaneous manifestations of secondary syphilis among young individuals. We would like to highlight the need for the implementation of sex education among adolescents/young adults to prevent STDs/STIs.