The issue of sex, virginity and marriage has been an important issue in many societies may they be traditional or modern. The issue 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 get married. So the first night with her husband is a purpose to sex. This made parents not to speak of sex to their children for fear not to make them know about it and abuse before the time they expect in order to keep their honour and the one of their daughter. Although this practice is not observed in European countries, it a great 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 responsible use of sex outside marriage through William Shakespeare’s All is well that ends well.