The protagonist of the novel, Orlando is a wealthy nobleman who is adventurous and artistic. Based on Woolf's real-life love interest Vita Sackville-West, Orlando (like West) has values deeply rooted in his home and in his long and noble ancestry. By changing genders halfway through the novel (from male to female) Orlando is able to reflect upon the differing positions and experiences of each gender. S/he is a reflective individual, who longs both for life and for love, and finds in poetry one of her greatest satisfactions. Orlando does not feel constrained by any time but the present, which frightens her in its potential for danger. It is in the present that Orlando realizes herself to be composed of not one, but many selves. Together, these selves and experiences combined with her love of nature, allow Orlando to find composure and confidence as one individual.
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Sasha is a Russian princess, a Muscovite, who travels by ship to England to the court of King James I. Her language and her demeanor makes her appear mysterious to the men of the Court, but her fluency in French allows her to converse freely with Orlando. When Orlando first catches sight of her, he is unable to tell whether she is a man or a woman. Her height and clothes make her appear androgynous, but Orlando is overcome her seductive nature. Deceitful, Sasha uses Orlando to entertain her while in London, and then she runs away with a Russian seaman, breaking Orlando's heart. The memory of Sasha's mysteriousness and seductiveness remains with Orlando as long as he lives.
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A brave, gallant seaman, Shel sweeps Orlando off her feet in the nineteenth century when he sees her hurt on the moor. Shel is in love with Orlando and hastens to marry her, but he, like many fictional Victorian heroes, is torn between love for a woman and his duty as a seaman. When the wind changes, he must return to his ship to sail around Cape Horn. Shel is loved by Orlando as well. He and Orlando are unique since they have many qualities of the opposite sexes. The narrator notes that he is "as strange and subtle as a woman," yet he commits the heroic acts of a man.
The Archduchess Henrietta who Orlando first sees riding on a horse through the courtyards of his home, is really a very tall man who dresses as a woman because he is in love with Orlando (as a man). He is a Romanian archduke of Finster-Aarhorn and Scand-op-Boom, and he asks Orlando to marry him and come away with him to Romania. As a character, he is ridiculous, a parody of heroes in novels who fall madly in love and do silly things to have their love requited. The Archduke is also quite slow; Orlando must cheat at a game they play over twenty times in order for him to catch her. Harry is traditional; he seeks a wife to live with him in his home, and he is appalled that a woman would cheat at a game. He plays a very comic role in the novel.
Nick Greene appears twice in the novel, once as a seventeenth-century poet who writes a parody of Orlando, and later as the most eminent Victorian (nineteenth-century) literary critic. But though times have changed, Nick does not change much at all. He is forever complaining about how the high-point of English literature has passed and how the authors of the current moment care only about money. He is generally an unhappy man, completely enraptured by his own ill-health. Greene is a perpetual literary critic who can tear down the work of others, but creates nothing of very much importance himself. Because he lives deep in the world of fame and good reviews, Greene is able to get Orlando's work published and made famous.
In real life, Alexander Pope, a poet of the eighteenth-century, was famous for his polemical satires and mock-epics, "The Dunciad" and "The Rape of the Lock." In the novel, Orlando places Pope on a pedestal when she meets him at a gathering of "brilliant" people. When Pope is the only one to say truly witty things at the gathering, Orlando becomes enraptured by him and the fact that he is a writer. But the description of him is quite unflattering, "he looked like some squat reptile set with a burning topaz in his forehead." Orlando finds that Pope is a regular person, driven by petty jealousies, praise, and ego, like every other writer.
The old gypsy man of the tribe in the hills of Turkey, Rustum welcomes Orlando into the tribe, but later distrusts her when he finds her beliefs differ so much from those of the gypsies. As a gypsy with no "official" property or ancestry, but whose lineage stretches back thousands of years (far further than Orlando's), Rustum cannot see the point in taking pride in a house of 365 bedrooms. To him, such a thing is worthless because it is not necessary. He does not see nature for its beauty (like Orlando) but for its potential to do danger. Ultimately, he functions in the novel to give Orlando perspective on her English values.
Queen Elizabeth is a noble, older woman who is very accustomed to having power and control. She takes likes Orlando for his youthful, innocent look, something she longs to regain for herself. After she makes Orlando her Treasurer, Steward, and lover, she grows possessive of him. Her nature will not allow her to accept that she should be tossed aside for another. Violently jealous, Elizabeth cannot handle that Orlando would choose another lover. She dies soon after seeing him with another woman.
A Spanish woman in Turkey, Rosina's marriage to Orlando lasts only a day before Rosina falls into a deep trance. Rosina does not play a major role in the novel, but the reader learns that she is a Spanish dancer, reputed to be a gypsy, whose mother and father are unknown. Her character is thought to be based on Vita Sackville-West's grandmother, who was a Spanish dancer.
One of the first women Orlando dated when he was a member of King James's court, Clorinda was a sweet, gentle lady, but her excessive religiosity and her intentions to lead Orlando from a life of sin, sickened him.
The second of Orlando's loves at King James's court, Favilla was the daughter of a poor Somersetshire gentleman. Though Favilla had excessive grace and was greatly admired at Court, Orlando ended their relationship when he saw her whipping a spaniel dog.
The third of Orlando's loves at the court of King James, Euphrosyne would have made the perfect wife of a nobleman. She was fair, sweet, kind to animals, and from an extraordinarily good Irish family. Plans were under way for the marriage between Orlando and Euphrosyne, when he decided he preferred to run away with Sasha.