The series of five paintings is based on the novel Orlando: A Biography that Virginia Woolf wrote in 1928. It is a biographical autofiction and is considered a love letter dedicated to her girlfriend Vita Sackville-West.

In The Great Frost. Frozen Thames speaks of heartbreak alluding to the scene in which Orlando is abandoned by his beloved Sasha. This idyll took place during The Great Frost, a harsh winter that took place in England during 1608-09 where the Thames came to freeze. Hence that hole appears at the bottom and an orange-haired figure (Orlando as a man) is willing to jump on a trampoline and avoid despair over the abandonment of his beloved.