What are positive and negative lessons about love learned from the characters in Shakespeare's Twelfth Night?

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Twelfth Night is one of the greatest plays ever written about love. Many of the characters do gain new insights through losing their hearts. And while Shakespeare certainly doesn’t set out to be didactic, audiences listening to his words may also learn some very human truths. Are these “lessons” positive or negative? That depends on your perspective. There’s a lot to be said on this topic. Here are a few ideas to get you started:

Viola: The first thing we learn about Viola is that she and her brother Sebastian have just been shipwrecked. Viola has been miraculously rescued, but she’s in anguish at the thought that her beloved brother may have drowned. Because she cares so much, she must struggle with this terrible dread until almost the end of the play.

Viola hatches a scheme to disguise herself as a young man (“Cesario”) and join the court of Duke Orsino, the ruler of Illyria. In her very first scene, Shakespeare foreshadows the fact that she is going to fall in love with her new employer. When she hears the duke’s name, Viola recalls her father mentioning it to her long ago:

VIOLA
Orsino! I have heard my father name him:
He was a bachelor then.
                                        [I.ii]

In what context, we wonder, did Sebastian Senior mention Orsino to his young daughter, and inform her that the duke was unmarried? Could it be that he was considering Orsino as a possible husband for Viola?

Viola does fall for the duke, and finds herself trapped in a dilemma: she can only serve him as long as she maintains her disguise, but as long as Orsino believes she’s a boy, he will never see her as a woman. Even worse, Orsino is infatuated with Olivia, and sends “Cesario” off to woo the beautiful countess on his behalf. The devoted Viola finds herself using all her eloquence to persuade Olivia to marry the man whom Viola herself loves.

If Viola didn’t know it before, her experiences in Illyria teach her that deep love makes us vulnerable to pain. One reason her character is so appealing is that, despite all the suffering that she experiences, she continues to love Sebastian and Orsino with absolute devotion.

Olivia: Olivia, too, is already grieving at the start of the play. She’s in mourning for her father and her brother, who have both died recently. While we may suspect that she’s using her bereavement as an excuse to keep Orsino at arm’s length, there’s no reason to think that her grief isn’t real:

VALENTINE
The element itself, till seven years' heat,
Shall not behold her face at ample view;
But, like a cloistress, she will veiled walk
And water once a day her chamber round
With eye-offending brine: all this to season
A brother's dead love, which she would keep fresh
And lasting in her sad remembrance.
                                                   [I.i]

Olivia herself has never been in love. She finds Orsino’s suit irritating, and she has no real empathy for him. Viola finds Olivia’s coolness infuriating:

VIOLA
Love make his heart of flint that you shall love;
And let your fervor, like my master's, be
Placed in contempt! Farewell, fair cruelty.
                                                [I,v]

Little does Viola realize that Olivia has...

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