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As a woman, Viola discovers that she can find no work, a situation Shakespeare fashions to coerce Viola's creation of Cesario. Shipwrecked in Illyria, Viola initially wishes to gain employment with the Countess Olivia in her own shape as a woman, though without disclosing her name and station; Olivia's mourning makes a suit to her impossible, empowering Viola to conceal who she is and seek service instead with Duke Orsino in the guise of the youth Cesario (Garber 1992, p. 168). Not unlike Rosalind, Viola is trapped in her disguise when she falls in love with the man she serves and is sent by him to plead his love to Olivia (Ibid).
Like Rosalind, Viola also assumes the character of Cesario in order to protect her self-determination, the object of her desire being erstwhile out of her reach. Unlike Rosalind, Viola's abuse of her alter ego and manipulation of the situation between Olivia and Orsino involves the direct abuse of Orsino's trust in order to take the place of Olivia as Orsino's object of affection. Aiding and abetting Viola's project, however unintentionally, is Olivia, who in spurning Orsino's advances indirectly endorses Viola's pursuit of Orsino's affections. Unlike Rosalind's situation, Viola's likeness as a man closely resembles her twin brother Sebastian, accentuating the existence of society's dichotomous gender system. Sebastian's absence from the opening of TN summons the possibility that Viola unwittingly replaces her brother, bringing to the forefront the familiar theme of primogeniture in AYLI. Where the two plays differ in this respect is Viola's direct transgression of the familial unit, whose gender roles are arguably more concretely established than those in the sexual male/female order. As a proxy for Sebastian, Viola goes on about her life as Cesario in order to survive, downplaying insinuations of malice in her cross-dressing venture. Using her forged identity to locate her brother later in the play, however, suggests that Viola's replacement of Sebastian earlier represents a violation of Elizabethan patriarchy. When Viola eventually finds work in the household of Orsino, she discovers a victim to another transgression existing separately from her own cross-dressing. The figure of Olivia almost defines the course of the play; Olivia is the tempest to conquer in TN, a jilted lover who refuses to succumb to the throes of amorous endeavours. Unconquerable by Orsino, Olivia is a prototypical unruly woman of the likes of classical figures such as Grendel's mother.
With no man dictating her life, Olivia poses more of a transgression to the gender system of Elizabethan society than Viola, mirroring AYLI's Celia in her homoerotic tendencies toward Viola's alter ego Cesario. Upon wooing Olivia at Orsino's request, Viola inadvertently gains Olivia's affections as Cesario.