Compare and contrast the characters of Viola and Olivia in Twelfth Night.

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The most important qualities Viola and Olivia share in Twelfth Night are, first, their profound grief and, second, their opennness to folly and improvisation. Both women have lost their fathers, and both believe they have recently lost their only brothers. They are alone in the world and, as they are...

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The most important qualities Viola and Olivia share in Twelfth Night are, first, their profound grief and, second, their opennness to folly and improvisation. Both women have lost their fathers, and both believe they have recently lost their only brothers. They are alone in the world and, as they are young women, are likely making their own decisions for the first time. Olivia's choice is to withdraw from the world, ostensibly for seven years. In doing so, she ignores the natural call of youth, which typically draws—at least in Shakespeare—the person toward love. Viola withdraws into her male identity, seemingly denying her feminine youth as well, becoming something of a counterfeit Sebastian.

Viola immediately decides to improvise a life in Orsino's court. She is open to falling in love with him and is able to connect to all the various characters in Illyria. She accepts the madness of love and human existence but pushes forward. When she is forced to woo Olivia for Orsino, she does so as best she can, taking the wry perspective that she would rather be the wife of the man for whom see is seeking Olivia's hand. Similarly, Olivia, after Viola's "willow cabin" speech, falls in love, breaking her vows to not entertain others, especially regarding marriage proposals. She makes a fool of herself and, like Viola, admits that she is subject to folly. She persists nonetheless.

In these important respects, the women are quite similar. An important difference lies in Viola's role as a catalyst in the stagnant Illyrian world. Olivia likely would not have grown or abandoned her grief were it not for Viola's accidental presence in this world. She would likely have fulfilled her vows and become more entrenched in her absolutism, much as the rest of her household is entrenched in theirs: Malvolio (strict puritanical order), Toby (excessiveness). Viola proves a change agent for all.

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Both Olivia and Viola are women of high social status who have recently lost (or believe they have lost) their brothers. Though they are similar in background, their responses to the deaths of their loved ones are quite different. While Olivia's grief has forced her to close up the doors of her home and admit no suitors, Viola's grief and sudden change in circumstances force her to disguise herself as a man and go into service for Count Orsino, pretending to be both a different gender and a different class.

Another similarity between the women is that both Olivia and Viola's mourning periods are interrupted by an unexpected infatuation. Olivia is snapped out of mourning by the onset of her love for Cesario, while Viola's grief is given almost no stage time before she begins pining for Orsino.

Finally, though Olivia initially holds a cynical view of love, she is almost immediately swayed by Viola/Cesario's overtures of love, proving that both women are romantics at heart.

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Both Viola and Olivia are women who belong to the aristocracies of their respective communities. They are "gently bred" and educated in womanly arts rather than in such masculine skills as swordplay and classical languages. Both, at the time of the play, are young, single, and attractive. Both have or had beloved brothers, but while Olivia's brother is actually dead, Viola's has merely been separated from her by a storm, although it takes them some time (and many comic plot twists) to be reunited. 

That being said, the two young women differ greatly in character. Olivia has become distraught over the death of her brother, while in adversity Viola displays great strength of character and intelligence. Olivia seems more conventional than Viola and also more emotionally melodramatic, while Viola has greater self-control and sense of purpose. Despite this, Olivia at times displays flashes of insight, as when she dismisses praise of her appearance with an inventory of her beauties: 

Item, two lips, indifferent red; item, two grey eyes, with lids to them; item, one neck, one chin, and so forth.

This suggests that, as a wealthy young woman, Olivia has learned to take a somewhat cynical view of her suitors, seeing that they are interested only her her appearance or wealth, and her being attracted to Viola's kindness and intelligence actually does suggest good judgment.

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Viola and Olivia are both gentlewomen raised to self-esteem, manners, breeding, wealth and luxury (Olivia more so) who both recognize and accept the role of Fate in their lives. This is where their character descriptions part company. Olivia's overriding trait is emotional foolishness. Her brother has recently died after a good religious life because Feste declares him to be in "heaven." Olivia's response of mourning is to mourn for seven years with her face under a veil while refusing all declarations of love and weeping daily.

Viola, in contrast, has lost her brother and takes the encouragement offered by the Captain to hope for the best results for her brother. She accordingly develops a plan for coping with life without her brother and pursues it, even though it is certainly a plan for life that she never would have thought of prior to her loss. Both women fall in love at first sight, but Viola falls only once whereas Olivia falls once and switches once when she marries Sebastian. Speaking of which, Viola seems to have made the worse choice in her object of affection while Olivia seems to have made the better choice: Orsino is emotionally volatile and changeable whereas Sebastian is Viola's twin, which suggests her twin in character traits also.

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