Virginia Woolf s thought provoking novel Orlando is considered the longest and most charming love letter in literature . It elatedly exemplifies the character of Orlando as the fictional embodiment of Woolf s close friend Vita Sackville-West. A dense novel which moves through three centuries, with each a transformation of the protagonist, from a man to a woman, portraying gender identity, expression and conformity. In every situation and adventure, Orlando carries with him the manuscript of his poem The Oak Tree . The poem. serves as a subject to brace his heart, the one thing which bridges all his selves together, from beginning till ending.