More than in any other Shakespearean play, the characters in Twelfth Night display a remarkable degree of gender and sexual ambiguity. Antonio’s passionate devotion to Sebastian can be read as homoerotic, or at least romantic. Lady Olivia falls in love with Viola, who is dressed as a man, but still resembles a woman. Duke Orsino is happy to shift his friendship with Cesario to romantic love once he learns Cesario is really Viola, but seems in no hurry for Viola to take off her male disguise. While Shakespeare and his contemporaries did not talk about sex and gender using the words and categories we would today, Twelfth Night self-consciously creates humor and enjoyment for the audience out of the possibility of unexpected attraction. Ultimately, the play is perhaps best understood as a testament to the unpredictable power of erotic desire and love in general.

In Twelfth Night, Viola dresses as the male Cesario in order to gain entry into Orsino’s court. In Elizabethan England, women were not allowed to act professionally, and female parts were all performed by men, so Viola would have actually been played by a male actor, dressing as a woman dressing as a man. The actor would most likely have been a young, androgynous-looking boy, since Cesario’s feminine characteristics are often commented upon. In fact, Cesario’s unthreatening masculinity convinces Olivia to see him in the first place. As Malvolio notes when first introducing him, he is “not yet old enough for a man, not young enough for a boy…One would think his mother’s milk was scarce out of him” (I.v.). Orsino believes Cesario’s more feminine appearance will help endear him to Olivia: “I know thy constellation is right apt for this affair” (I.iv.). This quote suggests Olivia may prefer young, feminine-looking boys to grown men like Orsino.

Just as Viola’s male disguise enables her to get close to Lady Olivia, dressing as a man allows Viola to experience a great degree of intimacy with Duke Orsino. Orsino and Cesario have candid conversations about love and relationships, and Orsino seems to highly value Cesario’s opinions. The play also suggests that Orsino’s feelings extend beyond friendship, even before he learns Cesario is really Viola. Possibly his attraction stems from the fact that Cesario still has feminine attributes even when dressed as a man – as Orsino says, “all is semblative of a woman’s part.” Another possibility is that Orsino is attracted to both the feminine and masculine aspects of Cesario. He is devastated when he thinks Cesario has married Olivia, but seems remarkably unruffled when he learns that the servant he has been confiding in is actually a woman. Rather than getting angry with Viola for deceiving him, Orsino seems delighted, saying “I shall have share in this most happy wreck.” (V.i.) Yet he continues to address Viola as “boy” or “Cesario” even after he knows Cesario is really Viola.

Perhaps the most overt references to homoeroticism in Twelfth Night come from the relationship between Sebastian and Antonio. While Sebastian doesn’t indicate that he has romantic feelings for Antonio, Antonio often expresses his adoration and love for Sebastian. The intensity of his feelings seems to imply erotic interest, as when he tells Sebastian “I could not stay behind you. My desire, / More sharp than filed steel, did spur me forth.” (III.iii.). However, audiences in Shakespeare’s day might have read Antonio’s declaration differently, as close male friendships were not unusual in Elizabethan England. In fact, in Shakespeare’s day women were thought to be intellectually and emotionally inferior to men, so a bond between two men would have been a bond between equals. Just as we can’t know how Shakespeare intended audiences to interpret Olivia and Orsino’s love for Cesario, we can’t know if he wants us to understand Antonio’s feelings as sexual desire, or passionate friendship. Regardless, Twelfth Night presents us with many versions of love, and suggests love, in all its forms, is an overwhelmingly powerful force that characters are helpless to resist.

Read more about references to homoeroticism in Oscar Wilde's The Picture of Dorian Gray.