Sir Toby and Sir Andrew stay up late drinking in Olivia’s house. Feste appears, and Sir Andrew compliments the clown on his singing. Both noblemen encourage Feste to sing another song. While he sings, Maria enters, warning them to keep their voices down or Olivia will call her steward, Malvolio, and tell him to kick them out. But the tipsy Sir Toby and Sir Andrew cheerfully ignore her.

Malvolio comes into the room. He criticizes the men for being drunk at all hours of the night and for singing so loudly. He warns Sir Toby that his behavior is intolerably rude and that, while Olivia is willing to let him be her guest (since he is her uncle), if Sir Toby does not change his behavior, he will be asked to leave. But Sir Toby, along with Sir Andrew and Feste, responds by making jokes and insulting Malvolio. After making a final threat, this one directed at Maria, Malvolio leaves, warning them all that he will let Olivia know about their behavior.

Sir Andrew suggests challenging Malvolio to a duel, but Maria has a better idea: to play a practical joke on him. As she explains to Sir Toby and Sir Andrew, Malvolio is a puritan, but at the same time his biggest weakness is his enormous ego: he believes that everybody loves him. Maria will use that weakness to get her revenge on him for spoiling their fun. Since Maria’s handwriting is almost identical to Olivia’s, Maria plans to leave letters lying around that will appear to have come from Olivia and will make Malvolio think that Olivia is in love with him.

Sir Toby and Sir Andrew are amazed by Maria’s cleverness, and they admire the plan. Maria goes off to bed, planning to get started on her joke the next day. Sir Toby and Sir Andrew, deciding that it is now too late to go to sleep, head off to warm up more wine.

The next day, at Orsino’s house, Orsino discusses love with his young page, Cesario (still Viola in disguise). Orsino tells Cesario that he can tell by looking at him that Cesario is in love. Since Viola is really in love with Orsino, Cesario admits that Orsino is right. When Orsino asks what the woman he loves is like, Cesario answers that she is very much like Orsino—similar to him in age and features. Orsino, not picking up on his page’s meaning, remarks that Cesario would be better off loving a younger woman, because men are naturally fickle, and only a younger woman can keep them romantically satisfied for a long time.

Meanwhile, Orsino has sent for Feste, who apparently moves back and forth between the houses of Olivia and Orsino. Feste sings another very sad love song (this one about someone who dies for love), and, afterward, Orsino orders Cesario to go to Olivia again, pleading Orsino’s love to her.

Cesario reminds Orsino that Olivia has denied his advances many times before, suggesting that Orsino accept that Olivia is not romantically interested in him, just as a woman in love with Orsino but whom Orsino did not love would have to accept his lack of interest in her. But Orsino says no woman can love with the same kind of passion as a man. Cesario disagrees and tells the story of a woman he knew who died for the love of a man: the woman never told the man about her love but, instead, simply wasted away. Cesario refers to this girl as her father’s daughter—leading Orsino, -naturally, to think that it must be Cesario’s sister. He asks if the girl died of her love, and Viola answers ambiguously. Orsino then gives her a jewel to present to Olivia on his behalf, and she departs.

These scenes give us the first of the play’s many songs. Twelfth Night is full of music, which is linked to romance from Orsino’s command in the play’s very first line: “If music be the food of love, play on” (I.i.1). Most of the songs are sung either by the drunken Sir Toby and Sir Andrew or by Feste the clown, who is a professional singer and entertainer as well as a joker. In Shakespeare’s time, love was often associated with the emotional expressiveness of music, so the love songs in this comedy are quite appropriate.

The clash between Malvolio on the one hand and Sir Toby, Sir Andrew, and Maria on the other is a central conflict in Twelfth Night. On the face of things, it does not seem to be Malvolio’s fault that he has to break up their party. After all, the men’s drunken singing in their host’s house in the middle of the night is unquestionably rude. But Twelfth Night is a play that ultimately celebrates chaos—whether it is brought on by romantic ardor, by alcohol, or simply by general enthusiasm—over the straitlaced order that Malvolio represents. The play’s title refers to the Feast of the Epiphany, the twelfth day after Christmas, which in Shakespeare’s England was a time for revelry and even anarchy—a day when servants impersonated their masters, alcohol flowed freely, and all of the customary social hierarchies were turned upside down. The puritanical, order-loving, and pleasure-hating spirit of Malvolio contrasts greatly with this anarchic spirit that flows through Sir Toby and Maria, Feste, and Sir Andrew. Malvolio, we realize, does not merely object to the circumstances of Sir Toby’s revelry—he objects to revelry, music, and alcohol entirely. His sharp questions—“Do ye make an ale-house of my lady’s house?” (II.iii.80–81)—prompt a bitter retort from Sir Toby, who asks. “Dost thou think because thou art virtuous, there shall be no more cakes and ale?” (II.iii.103–104). Sir Toby seems to understand Malvolio’s attitude: because Malvolio himself detests merrymaking, he thinks that no one should be allowed to make merry. His very name consists of elements—“Mal” and “volio”—that essentially mean, in Italian, “ill will,” suggesting his profound contempt for others’ pleasures.

Maria, however, proves more than a match for Malvolio. She knows his faults well: for one thing, he is a hypocrite, always trying to impress other people; worse, he is puffed up with pride, a weakness that she plans to take advantage of in exacting her revenge. Her comment that “it is his grounds of faith that all that look on him love him” (II.iii.134–135) remind us of Olivia’s earlier comment that Malvolio is “sick of [meaning “sick with”] self-love” (I.v.77). Maria’s trust in the all-consuming nature of Malvolio’s egotism leads her to believe that it will be easy to make him think—foolishly— that Olivia loves him. The revenge seems appropriate—Malvolio, who loathes folly, will be tricked into displaying it.

The dialogue between Orsino and the disguised Viola in Act II, scene iv further develops the curious relationship between Orsino and his seemingly male servant. Their discussion of the relative power of men’s and women’s love is one of the most often-quoted passages in the play. The complicated ironies built into the scene—in which the audience knows that Cesario is really a woman in love with Orsino but Orsino remains unaware—add both a rich complexity and a sense of teasing to the discussions, even as the seeming hopelessness of Viola’s position adds a hint of pathos. Still, one cannot find her plight too pathetic—the audience knows that the play is a comedy, in which romantic love must lead to married happiness. Moreover, we have already heard Orsino’s comments to Cesario in Act I, scene iv, praising Cesario’s female-like beauty, so we know that Viola’s disguise has not entirely prevented Orsino from being attracted to her.

Orsino’s claim that men love more strongly than women was a commonplace one in Shakespeare’s day, but Viola eloquently refutes it. In a very famous passage, she tells Orsino about how her fictional sister

“Patience on a monument” refers to statues of the allegorical figure of Patience, which often adorned Renaissance tombstones. By comparing her imaginary sister to this stone figure, Viola subtly contrasts her own passion with the self-indulgent and grandiose lovesickness from which Orsino claims to suffer. She depicts herself as bearing a love that is, unlike the duke’s, patient, silent, and eternally enduring. Of course, the image of a tombstone suggests that such a love is ultimately fatal, leading to Orsino’s question—“But died thy sister of her love, my boy?” (I.iv.118). This question is appropriately left open: we do not know yet whether Viola will die (literally or metaphorically) of her love for Orsino, and so she can only respond, ambiguously yet cleverly, “I am all the daughters of my father’s house, / And all the brothers too; and yet I know not” (I.iv.119–120). We, like Viola (and like Orsino), must wait to see how this tangle of desires and disguises will unravel.