In Taiwan, Chinese traditions are compounded with a patriarchal social structure, forcing eldest daughters into a special role within the family. Unlike eldest sons, who are afforded additional power by their rank in the birth order, eldest daughters must bear more responsibilities than anyone of their siblings. Drawing from numerous interviews as well as the author’s personal experience, Eldest Daughter Syndrome exposes a commonplace form of oppression in contemporary society, while also exploring how the personality type of the “responsible child” manifests on other levels of society. An overdeveloped sense of responsibility can introduce unfairness into relationships and takes a toll on the body and mind. However, if one is to have any chance of resolving this issue, one must dig deep, investigating the core of the personality type, as well as its genesis.