The 16th century marked the beginning of the fight against sexually transmitted infections (STIs) with the use of the male condom. However, many puzzling questions and prospective solutions have surfaced over the years in the context of condom use. In 1978, a condom riddle introduced the dilemma of a man having two condoms to use for intercourse with three consecutive women. In this paper, we will discuss the solution proposed to the aforementioned riddle, and examine its public health implications. Moreover, we illustrate the challenges involved in condom use and reduction of STI acquisition.