This chapter explores loneliness within girls’ school and college stories in the first half of the 20th century in the United States and Britain. It draws on examples from L.T. Meade, Angela Brazil, Elinor Brent-Dyer, Josephine Chase (Jessie Graham Flower and Pauline Lester), Dorita Fairlie Bruce and Ethel Talbot. The stories identify two nuanced aspects to the construction and experience of loneliness: first, the loneliness that is self-imposed by those who do not wish to conform; second, the loneliness that was imposed either on a newcomer or by one existing group on an individual member who appeared to transgress dominant forms of behaviour and community values. Representations of adolescent female loneliness remain remarkably consistent in stories across time and place.