The issue of sex, virginity, and marriage has been an important issue in many societies may they be traditional or modern. The situation becomes a national challenge when it has to do with young men of both sexes. Nowadays, many young men more or less of sixteen years old are already sexually active. In some African societies, before the wedding ceremonies, there was a step called linen ceremony aiming to control whether the woman was virgin before she gets married. So the first night with her husband is a purpose to sex. This gets made parents not to speak of sex to their children for fear not to make them know about it and abuse before the right age in order to preserve not only the honor of the family but also the one of their daughter. Although this practice is not the case in some European countries, it is a wonderful pride for parents to marry their daughter knowing that she preserves her virginity. But nowadays things have significantly changed. Sexuality, which has been a core of many taboos in many societies, is no more hidden. It seems while to be an act of no boundary, no age. It has become a source of many worries, from parents. This article, therefore aims at addressing the issue of Virginity, Sex and Marriage in general and Benin and British young men in particular with the emphasis on the challenges towards a right use of sex outside marriage through William Shakespeare’s All is well that ends well.