The character of Olivia in Shakespeare’s classic comedy Twelfth Night; or, What You Will is one of his more complex comic heroines, because of the inner conflict raging within the character after she falls in love with what she thinks is a young servant named Cesario (but is in fact a young woman named Viola in disguise).

As Kenneth McLeish and Stephen Unwin have noted, the character of Olivia is both the double and the opposite of Viola. They are both women who are simultaneous liberated and restricted by the action of the play: Olivia is liberated by her realisation that she loves Cesario (really Viola dressed as a boy), but she is restricted by her inability to know what to do with her feelings, and her reluctance to break out from the role she adopts at the beginning of the play – that of dignified mourner for both her father and brother – and confess her excited love for Cesario. Dramatic irony, i.e. what the audience knows but Olivia doesn’t know at this point, adds another restriction: the youth she has fallen in love with, Cesario, is really a young woman, someone she can never have.

The way the character of Olivia has been portrayed in productions of Twelfth Night has changed from production to production, and the change has been more pronounced than it has been in the case of most of Shakespeare’s other comic heroines. Until the beginning of the twentieth century Olivia was usually played as a stately Countess, with dignity and refinement, but more recently the character of Olivia has often been portrayed as a young, foolish girl. One of the most successful Olivias of recent years was actually played by a male actor, Mark Rylance, at Shakespeare’s Globe in 2012. Rylance imbued Olivia with a sense of decorum and primness, so that in the scenes where Olivia becomes carried away by her strong feelings for Cesario, the contrast is all the more noticeable (and all the funnier for it).

Olivia stands out in Twelfth Night because of her reluctance to take part in the frivolities involving the other characters. Sir Toby Belch, Sir Andrew Aguecheek, Maria, and even Viola, are all marked by their sociability with the other characters, whether it’s Sir Toby, Sir Andrew, Maria, and Fabian uniting to play their trick on Malvolio, or Viola deliberately adopting a disguise to get closer to Orsino. The two characters Olivia most closely mirrors are Orsino and, perhaps surprisingly, Malvolio. Orsino begins Twelfth Night pining away for Olivia; Olivia begins the play in mourning for her brother and father. But like Malvolio, Olivia’s cool, placid exterior is threatened by her more playful, foolish side when she falls in love with Cesario. Similarly, Malvolio is transformed from a stern steward into a smiling, yellow-stockinged and cross-gartered would-be suitor to Olivia when he is gulled by the other characters into believing he has a chance with Olivia. Both are deceived: Cesario doesn’t really exist, and Olivia doesn’t really fancy Malvolio.

The difference is that Olivia will, thanks to her chance meeting with Sebastian, get her Cesario, while Malvolio is destined to be thwarted in his desires. But then Olivia’s girlish giddiness when she falls for Cesario is utterly genuine, whereas Malvolio’s smiling exterior is just another disguise, designed to please the woman he believes he stands a chance of wooing.