As already mentioned, in Shakespeare 's times the man had the upper hand when it came to love, courtship and marriage. The woman, the submissive vessel, had to abide by the decisions made by her father or brother. Yet, in Twelfth Night these gender roles seem to be re-written, in some respects. Olivia 's wooing of Cesario would be one such instance. Sir Toby tells Sir Andrew of his niece that she has sworn not to marry anyone above her in station, age or wit. He is, ofcourse, not a very reliable source, but if his words are true then Olivia seems to be as determined as any man to marry the one of her choice. This could account for her reluctance to accept the Duke, who is accounted by all to be a good man. Financially independent, she is relatively free to pursue her ends as both her father and brother have died and her uncle is her dependent.
It does not take Olivia very long to discard her mourning weeds to pursue Cesario, which shows that this was only a pretext to keep Orsino at bay. Interestingly it is not Cesario 's 'masculinity ' that is appealing to Olivia. She finds his “beautiful scorn” and and “angry lips” (epithets more suited for a girl than a man) attractive . She tells him that she
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It is a Gordian knot, until the appearance of Sebastian. Like the Deus ex machina of the Greek plays all the problems are now resolved. Olivia cannot have the lover of her preference as that turns out to be a woman. She gets the next best thing- a man who is an almost replica of her Cesario. The Duke is suddenly left without an ideal and his only hope of finding love is to settle for the woman who loves him. This he does with surprisingly good grace. Thus, everything is settled happily. The men (Orsino and Sebastian) have done little in pursuing love, are chosen by their respective partners and have only to consent to the