Should you follow your heart or your head? That Girl in Pinafore is a coming-of-age tale set in 1993, Singapore, about dreams, friendships, and first loves. The story follows four teenagers' efforts to bring business back to a struggling folk music pub, and the blossoming love between Jiaming and May, both fans of Singaporean folk music.1992 - Singapore is on the verge of electing its first President, and chewing gum has been banned. Hope and rejuvenation is in the air, everyone believes in the Singapore Dream. Young musicians strive to give birth to a local music industry, creating local music at a rapid pace. Music cafes spring up everywhere alongside the hot new trend, karaoke. Jiaming is a free spirited teenager who has never taken school seriously. His parents own a music pub called 'Meng Chuan', and Jiaming feels schooling is useless as he wants to help out at the business. True enough, Jiaming flunks his 'O' level exams and drops out of school. Jiaming's buddies Caogen, Haoban and Xiaopang pass their exams and move on to Junior College. But they are caught renting porn magazines by the principal and are suspended for a month. During this month, the boys take part in a local music competition, have a taste of first love, and work hard to bring business back to the struggling 'Meng Chuan'.This coming-of-age tale sees Jiaming and gang learn the harsh realities of pursuing dreams in the real world. In growing up, the boys learn that choosing between your heart and societal expectations is akin to losing your innocence to the adult world. The eventual closure of the pub 'Meng Chuan' paralells the real world demise of the 'Xinyao' movement around the mid-90s. It signifies the lost of youthful innocence to the necessities of growing up.