Orlando's story spans four centuries and two genders, yet the character changes very little from his/her early years as part of Queen Elizabeth I's court. Throughout his/her long life, Orlando prefers nature to people and holds poetry above all else. He/she spends nearly her entire life working on one poem, "The Oak Tree," which serves as an evolving record of her thoughts and experiences. Orlando has close connections to the political and literary circles of the 16th through 19th centuries and experiences, but finds love and happiness to be fleeting. She has a particularly difficult time during the Victorian era, when marriage seems to be almost required of every man and woman. Orlando feels this goes against the rules of nature and attempts to become "nature's bride," then reverses her position the moment she meets Shel. With Shel, who was once a woman, Orlando finally feels understood and complete. She is able to finish her long-worked poem and unite all of her disparate experiences into one true self.
Orlando meets Russian Princess Marousha Stanilovska Dagmar Natasha Iliana Romanovitch at the king's court during the Great Frost. The only language they have in common is French, which no one else seems to speak. Orlando quickly becomes besotted with the princess, whom he nicknames Sasha after a pet fox that once bit him. Sasha is not impressed with Orlando's bouts of melancholy and depression, and she has very few niceties to say about the English court. Her dismissive air only fuels Orlando's adoration. Though he is never quite sure about her feelings for him, he is completely obsessed with her. Years later, when Orlando turns into a woman, she can understand Sasha in ways she couldn't as a man.
Marmaduke Bonthrop Shelmerdine is a former soldier and sailor whose life's ambition is to sail around Cape Horn. He stumbles upon Orlando in the park, and they immediately recognize kindred spirits in one another and become engaged. He, like Orlando, started life as the opposite gender, which is perhaps what makes them such a good match. He doesn't mind when she disappears into the woods to enjoy one of her contemplative moods, and she doesn't question his dedication to life at sea. They make one another feel whole.
Orlando invites Nick Greene to his country home to talk about Orlando's poetry, but the snide and low-class Greene is more interested in talking about himself and the death of literature. Nearly 300 years later, Greene has risen through social and academic circles to become a man of importance and wealth. He despises the popular literature of the time and helps Orlando publish "The Oak Tree" because it has no trace of "the modern spirit."
Archduke Harry is from the Roumanian territory. He saw a portrait of male Orlando years before, immediately fell in love, and decided to move close to Orlando's country home, where he disguises himself as the Archduchess Harriet. Orlando is horrified by the archduchess's attentions and flees to Constantinople. When he returns as a woman, Harriet reveals himself as Harry and asks for Orlando's hand in marriage. Orlando finds Harry terribly boring—they have nothing in common and nothing to talk about. He remains loyal even when she cheats him out of money. Orlando finally gets rid of him by dropping a toad down his shirt. When they meet a few days later, he once more asks her to marry him.