What is the importance of the two songs in act 2, scene 3 of Shakespeare's Twelfth Night?

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The first song that the fool sings is to Sir Toby. The lyrics begin by addressing his “mistress mine,” which is Olivia, to ask where she is “roaming.” At this point in the play, Olivia is searching for love, but the song indicates love will come for her—in the form of Sebastian, as we learn later. However, the second verse suggests that her future is “unsure.” By the end of the song, it seems to suggest that she just needs to settle with whoever she has found already (Orsino), because her youth “will not endure.” Instead of holding out for the perfect lover, one should just take whoever shows interest, before they grow old. This song ultimately shows that those who search endlessly for love will not find it. Instead, they have to accept that love will find them.

The fool sings the second song at the behest of Orsino, who is feeling discouraged that Olivia has not yet returned his pledge of love. This song has a morose tone, with the speaker of the lyrics outlining his demands for his funeral and subsequent burial. The speaker says he has been “slain by a fair cruel maid,” meaning a beautiful woman has broken his heart. His final stipulation is that he be buried where one should “never find [his] grave/ To weep there!” This melodramatic song reflects Orsino’s feelings about his current situation. He truly believes that without Olivia’s love, he will surely die.

Each of these songs reflects the emotional state of Olivia and Orsino clearly, but they could also indicate Viola’s thoughts. As the fool performs the second song, Viola hints to Orsino that there is a strong woman who loves him just as much as he loves Olivia—meaning herself. According to these songs, Olivia and Orsino are both superficial in their view of love at this point in the play, but Viola is a dedicated, steadfast lover who is willing to sacrifice her own happiness if it means her beloved will be happy.

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The first song that Feste sings in Act 2, Scene 3 is a love song. Essentially, the song is about waiting for love. The first line speaks of a woman who is roaming about in search of her true love, while the second line tells the woman to wait because her "true love" is coming. The song further states, "Journeys end in lovers meeting," meaning that the search for love obviously ends when lovers finally meet each other. The first five lines in the song speaking of lovers meeting are particularly applicable to the theme of love found in the play. Both Olivia and Orsino are in search of love. Orsino thinks his journey for love will end when he finally wins Olivia, while Olivia feels hers will end when she finally wins Cesario. 

The final line in the song, "Every wise man's son doth know," is also particularly applicable to the theme of love, but more specifically to the theme of the foolishness of love. In fact, one of Feste's roles in the play is to illustrate the theme of the foolishness of mankind by showing how all the characters are foolish but himself. What is important about the final line is that it's saying it is the wise man's son who knows about love, not the wise man himself. Therefore, the final line is implying that lovers are very foolish. The theme of the foolishness of love is even illustrated by the behavior of both Orsino and Olivia. Orsino's foolishness is illustrated in his relentless obsession over Olivia, while Olivia's foolishness is illustrated in first her groundless rejection of Orsino and then the fact she falls in love with a man who is obviously not a real man due to his obvious feminine characteristics. Hence, Feste's first song is significant in that it embodies two of the plays themes, the quest for love as well as the foolishness of love.

The second song found in Act 2, Scene 3 is part of an English ballad that was popular in Shakespeare's day. It's sung between lines 94 through 104, and both Sir Toby and Feste take turns singing lines from the song. The song appears to be about death, but Sir Toby and Feste are wittily using it for other meaning. The first line, "Farewell, dear heart, since I must needs be gone," is used as a reference to Sir Toby's rowdiness (94). He is using it to refer to the fact that he is making a disturbance in the house and either needs to quiet down or leave the house. Then, Feste and Sir Toby both use other lines of the song to wittily tell Malvolio to leave them alone, such as, "Shall I bid him go?" (101). In general, the song is important in that it captures the festive, comic spirit of the play.

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