At her entrance, Olivia immediately instructs someone to "take the fool [Feste] away." She finds him to be a "dry fool" — that is, Olivia is in mourning, and foolery ill becomes her at this time. When the fool asks for permission to prove his lady a fool, she grants him permission to do so, and eventually Olivia appreciates the fool's wit and logic; in fact, she is sharp with Malvolio, who disparages the fool and wonders how his mistress can take delight in such a rascal. Again, Malvolio shows that he has no sense of humor; he constantly tries to keep the entire household in an atmosphere of gravity and oppression. His oppressive melancholy prepares the audience to take great delight in the trick that will be played on him later.
When Cesario arrives at the gate, notice that Olivia will have nothing to do with this messenger. Yet Olivia changes her mind about seeing the messenger when she hears the description of the youth given her by Malvolio, a description which whets her imagination; suddenly she desires very much to see him, but she is not anxious to reveal this in front of the dour Malvolio. Thus, we realize that Olivia's guise of mourning for her brother is only another of the many disguises that are employed during this comedy — that is, Lady Olivia used the excuse of her brother's death as a pretext for singling herself out and making herself interesting, and certainly news of her excessive mourning has been carried throughout the country, as we saw in all the preceding scenes.
When Cesario is admitted, further masks and disguises are used to their fullest. First, Olivia has a veil over her face which disguises her true appearance. Viola herself, of course, is in disguise as the young Cesario and, furthermore, as Cesario, she is playing a part because as Cesario, she has memorized a speech that is to be delivered to Olivia. Then, too, there is an abundance of play on words, constantly emphasizing how Olivia is usurping her own role and that Cesario wants only to present the heart of the message, which is to play on Olivia's heart, and when Cesario finally finishes his speech, he says that he holds an olive, the sign of peace in his hand. Note that "olive" is a derivation of Olivia's name and ultimately, by the end of this scene, Cesario will figuratively hold Olivia in "his" hands, since she will by then be enamored of the youth. Cesario must, of necessity, be a good wooer or else lose favor with Duke Orsino. Therefore, there is such a passionate intensity in his pleading that Olivia is struck not so much by the message (which is trite, old and hackneyed), but by the messenger (who is young, passionate, and good-looking). At the same time, Cesario senses that Olivia is too proud to be wooed by proxy, but he attempts to do so anyway. After the message is delivered, Olivia is oblivious to it, but she is so entranced by the messenger that she offers a purse filled with money. Cesario refuses the gift indignantly; he is no fee-accepting person: "I am no fee'd post, Lady; keep your purse. My master, not myself, lacks recompense."
