Personally I think that the pair of Viola and Olivia is possibly the most interesting a socially challenging of all the pairs found within Twelfth Night. In Viola and Olivia’s first encounter in Act I Scene V, Viola acts as Cesario. Through Violas disguise as a male, Shakespeare “challenges gender permutations, boy-girl, boy-boy, and girl-girl”. In this scene She preaches her master (Orsino’s) great romantic pretensions. However half way through Cesario breaks the poetic speech with an anticlimactic interjection of prose “I took great pains to study it and ‘tis poetical”. This immediately undermines her master’s message. Due to Viola is posing as a man she therefore simultaneously challenges both her gender and social role in this scene. By maintaining the pretence to be a man and through undercutting the Duke of Illyria’s speech as she is the “surrogate wooer”. The most ironic part of this first encounter however is the point that Olivia is actually more attracted to Cesario as Viola speaks in her own voice.

Due to Viola acting as Cesario in this first meeting with Olivia, it is no surprise that Cesario, being the “male” dominates the scene as in the 1600s society would be inherently patriarchal. However as Cesario is actually Viola this once again subtly challenges gender roles as she is leading the conversation. The fact that Olivia is a countess also reinforces this idea of Viola challenging the social hierarchy, although both characters speak in prose during this meeting, suggesting a comfortable and equal atmosphere. The speech takes on a more stichomythic form as the characters as the two engage in verbal sparring between 184-94 after Olivia’s first interruption of Viola/Cesario. This rally of speech takes a slightly erotic tern as Viola/Cesario invites Olivia to “unveil” herself – puns were popular, beloved by the Elizabethans’. As Viola is now speaking as herself it is unclear why she should ask Olivia such a thing, something that tests the gender expectations of the time. Due to this being a play during the Elizabethan Era, there is also the fact that women were played by male actors on the stage due to the patriarchal Renaissance society. Orgel suggests in response to boys playing female roles that “the age of the actor is as irrelevant as the gender: womanliness is simply a matter of acting” (Orgel 70). This early modern stage convention therefore adds yet another layer of complexity to this gender disguise of Viola as she is a three fold character – ingeniously comic to the Elizabethan audience and something that was revived with an all male production of Twelfth Night in 2002 at Shakespeare’s Globe.