The song "Shy" by Gilbert O'Sullivan tells the story of a shy and inexperienced young man named John. Every time he passes by the person he is attracted to, he feels inclined to look away, unable to express his feelings. One day, he promises himself that he will gather the courage to approach her and speak up. In the second verse, John imagines a scenario where he sees the person drop a glove. He contemplates asking her if the glove belongs to her, hoping to strike up a conversation. However, he anticipates her response to be dismissive, likely rejecting his attempt to interact. As the song progresses, John reflects on his lack of success with women his own age. Despite his ability to impress them with his taste in food and wine, he admits his immaturity and inexperience when it comes to love-making. He usually pretends to be tired and falls asleep as a way to avoid intimacy, showcasing his insecurity and fear of not living up to expectations. The chorus suggests that John is resigned to a life of loneliness, believing he is doomed to live in one room, metaphorically representing his emotional isolation. He spends his days dreaming of a fictional scenario where a famous actress, Sophia Loren, seduces him. This fantasy serves as an escape from his insecurities and provides him a sense of comfort. The song ends with John introducing himself as a twenty-one-year-old who drives a Ford Cortina estate. He playfully invites the listener to join him in his room, offering to show them his license plate as a way to demonstrate his limited excitement and lack of confidence in himself. Overall, "Shy" delves into the inner thoughts and struggles of a socially anxious and inexperienced young man, expressing his yearning for connection and his need for validation.