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Adolescence, as we all know, is one of the most complicated stages of one’s life. It is marked by psychological, cognitive, and physiological changes. The experiences and learning at this stage forms a soil bed, on which the plant of adulthood grows. However, what it grows into is the question. Young boys and girls are confused about the changes taking place at every level, and thus are vulnerable against long term problems like substance abuse, personality and mood disorders. Therefore, this stage can either ‘make you or break you’. This research paper looks specifically into the relationships of a young boy who is dealing with puberty, especially from sexual point of view. He is no longer a boy, but definitely not yet a man. There is a constant tussle between the two forces. It is during this phase that one’s sexuality, sexual preferences, sexual confidence etc are developed. Issues like homosexuality, Promiscuity, masculinity etc in men, have their roots in how an adolescent boy develops and learns in this crucial stage. Carl Gustav Jung understood its importance and has explicitly written on this theme. Not only this, his theories are finding their confirmations in the research that is being undertaken today. It becomes amply clear that sexual experiences in adolescence have far reaching consequences and affect our relationships in adulthood in more ways than we thought earlier.