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Viola as Cesario faced the most challenges in the play. It almost seems that fate never leaves her alone, as her difficulties start as soon as we are introduced to her, washed up upon the shores of illyria having barely survived a shipwreck. Alone in a foreign land with her only kin, her twin brother Sebastian believed to be dead, she is left to fend for herself for, or so it seemed, the remainder of her days.
For any young female, this would be a devastating situation to be thrown into, and viola was no exception. Apart from having to deal with the loss of her brother, she also had to find a way to survive in illyria. Perhaps this is where the resilience in viola's nature is first shown instead of breaking down and mourning bitterly the death of her loved one, she immediately devises a plan to disguise herself as a male and serve duke orsino.
But unfortunately for viola, fate was not on her side, and this disguise which was meant to assist her only turned out to be a bigger burden in time to come.
Complications also arose when viola fell in love with her master, duke orsino, while at the same time had the love interest of orsino, the countess Olivia, trying to woo her. This placed viola in an extremely difficult and complex situation on one hand, she loved the duke and would have liked to do all she could to win his heart. But because she was his servant, she was obliged to serve him and help him win the hand of Olivia. What was a poor girl to do ?
She was left confused, knowing that whatever she did would end up hurting somebody. Her kind and sensitive nature allowed her to sympathize with Olivia, and she declares what thriftless sighs poor Olivia shall breathe !'.
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Yet while trying to fend of olivia's constant admissions of love in a subtle and delicate way, she also had intense feelings for the duke, who, caught up in his unrequited love for Olivia failed to notice the hints that she continually dropped. It was a blow to viola for the man she loved to ignore her like that simply because he loved, or thought he loved somebody else.
As it is, admitting her love for orsino, albeit indirectly, must have taken courage, especially in Elizabethan times where women were not known for attempting to court men. Moreover, one can see from her descriptions that she is truly pining for the duke(only unable to show it in everyday life), she describes herself with green and yellow melancholy she sat like Patience on a monument smiling at grief'
Yet despite all her attempts, everything she said was cruelly shot down by the duke who claimed that there was no compare between that love a woman can bear me and that I owe Olivia'. Although he did not do it intentionally, his response must have caused much hurt to viola as her love was more or less rejected. And all this while, viola was forced to put up a front and pretend that nothing was wrong while working for the duke. Is it fair to subject a girl to all this ?
However being brave and matured for her age, we hear nary a complaint from viola throughout the play that her emotions and acts went unappreciated. Though she was young, perhaps she was the only character of the play who truly understood how loved worked that it was something rare and beautiful, and something that cannot be forced by one onto another no matter what. This may have been why she never complained or showed excessive sadness when the duke did not seem to reciprocate her feelings.
She also faced the obstacle of having to be in disguise all the time, an elaborate getup that altered her gender for as long as she was in it. Some way into the play, she comes to realize Disguise, I see thou art a wickedness' as it caused her much unhappiness and trouble. It impeded the development of many things, not least the development of the relationship between her and the duke much more quickly, had she come into his residence dressed a girl.
However once she had begun with the disguise, she was forced to stick with it until the resolution at the end of the play. It rendered her unable to confess her true love directly to the duke and have him potentially respond in kind without all the trouble of courting Olivia(which amounted to nothing anyway since it seemed that the love he claimed to be in was fired by his own imagination rather than Olivia's presence in his life)
Her disguise also was the cause of hurt feelings and seeming betrayal at the end of the play when the duke mistakenly thought she'd married Olivia when really, it was her twin brother who had done so. He even made to kill her for betraying him, and was willing to sacrifice the lamb I do love to spite a raven's heart within a dove'. This put her very existence at risk, and it was all due to the disguise.
But through everything, viola faced adversity bravely and was a constant exemplar of grace under pressure. She dealt with all the challenges that came her way better than most other characters in the play would have, and in the end, her happy ending with the duke is indeed well-deserved.