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Over at Olivia's place, Maria and Feste the Clown goof around, talking trash. Feste makes a dirty joke about how "well hung" he is when Maria tells him that Olivia will literally hang him (as in tie a noose around his neck and let him dangle in the air until he stops breathing) because he hasn't shown up to work in such a long time. (Feste's job as Olivia's "fool" is to be an entertaining smart-aleck. Imagine paying Dave Chappell or Will Ferrell to follow you around, crack jokes, insult you, sing some songs, and run your errands.)
Olivia enters and orders her servants to "Take the fool away." Feste responds by saying something like "Hey – didn't you hear Olivia say take the fool away? Take her away already."
Olivia is totally amused, but pretends she's not, so Feste will have to convince her that he should be allowed to stay and make her laugh. Then Feste makes a crack about why Olivia really is a fool – she's wasting her time mourning for a dead brother who's in a better place (heaven), while she mopes around in her crazy, all black get-up.
Malvolio enters the room and asks Olivia why she lets Feste hang around. Malvolio claims that Feste isn't really that funny and, besides, he saw some other comedian totally clown him the other day.
Olivia tells Malvolio to beat it – he's a bitter jerk if he doesn't see how great Feste is.
Maria enters then with news that there's some dumb kid at the gate who wants to talk to Olivia. He's not taking "no" for an answer and Maria doesn't know what to do.
Olivia tells Malvolio to go to the gate and say she's sick or busy or whatever. The kid should hit the road ASAP because she's not in the mood to talk.
Feste makes a random joke about how brainless Sir Toby Belch is, just as Olivia's uncle enters the room. Olivia then takes Toby to task for being a drunk and spending all his time partying. She also asks him about who's at the gate.
Malvolio reenters the room and confirms that, yep, there's an annoying kid at the gate who says he's not going anywhere until he sees Olivia.
Olivia asks what the messenger is like and Malvolio says that he doesn't seem old enough to be a man or young enough to be a boy. The kid also speaks like a "shrew." (That's code for mouthy woman.)
Intrigued, Olivia lets the kid inside, but not before she covers her face with her black veil.
"Cesario" enters the room and asks which one of the lovely ladies is Olivia – "he's" got to deliver a message from the Duke.
Olivia's not interested in the Duke, but the kid is intriguing so she chats him up. "Cesario" says "he's" got this whole message memorized, so Olivia should just please pipe down and let "him" deliver it.
Olivia's not interested in Duke Orsino's cliché attempts to sweet talk her, so she toys with "Cesario" for a while and asks why he was so lippy when he was out at the gate. "Cesario" insists that "he" needs to speak to Olivia alone so he can deliver his private message.
"Cesario" tries to deliver the memorized speech again, but Olivia cuts "him" off and mocks the Duke's little love letter.
"Cesario" asks to see Olivia's face and Olivia removes her veil.
"Cesario" says that Olivia is gorgeous – she should get married and have some good looking kids with Orsino.
Exasperated, Olivia says that the Duke already knows she's not into him. He's nice and all, and rich, and handsome, but he needs to learn to take "no" for an answer.
"Cesario" says that doesn't make any sense. Then Olivia asks "Cesario" what he would do if he loved her (Olivia) and "Cesario" says "he" would stand at Olivia's gate and sing love poetry until Olivia took pity on "him."
Olivia is totally smitten when she hears this and she asks "Cesario" about his parentage, to which "Cesario" replies that "he" is well-born.
Olivia tells "Cesario" to go back to Orsino and tell him to quit bothering her. Then Cesario should come back and tell Olivia what the Duke has to say about that. Olivia tries to give "Cesario" a few coins for his trouble, but "Cesario" tells her to keep her money.
When "Cesario" leaves, Olivia says "Cesario" is a total dream-boat.
Malvolio enters the room and Olivia lies and says that "Cesario" gave her a ring from the Duke. She says she doesn't want it so Malvolio should run after "Cesario" and return the trinket, ASAP.
Olivia has apparently forgotten about her quest to mourn for her dead brother. She tells us that "fate" has brought "Cesario" to her, so she'll let whatever happens happen.