Tea and Sympathy
This film, based on the stage play, is a symbol for the era. Men were meant to be macho, to enjoy sports, chase girls and be brave. This only turned into aggression and in many instances violence towards women and other men who were not like them who they labeled as effeminate. This film dispels those lies and is a symbol of the much needed change in the world from one of machismo led to one of uniqueness in individualism.
Laura
Laura spend time with Tom and eventually falls in love with him and sleeps with him. She leaves her husband Bill years later and this is a symbol that she, like many, bought into the machismo of the times by marrying Bill but truly wanted a man who simply knew who he was and sought to find his place in the world rather than fighting in it against anyone who was unlike him.
Novel
Tom writes a novel years after his experience at the prep school. The novel is a symbol of his capacity to take what was a hard experience in his life and turn it into something meaningful to speak for those, like him, don't buy into the machismo world and who have very few speaking up for one another.
Shaw
Tom reads Candida, a play by George Bernard Shaw, while his classmates plays sports and fantasize about girls. This is a symbol of Tom being an intellectual, someone who doesn't fit in with the crowd.
Prostitute
Tom goes to sleep with a prostitute in order to "enter manhood". This is a symbol of the unnecessary actions boys take in order to fit in with a crowd they don't even want to belong to in order to make the pain that crowd inflicts stop.