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Countess Olivia is the gorgeous heiress with no father, brother (they're both dead), or husband to tell her what to do or how to balance her checkbook. Characters like Duke Orsino, Sir Andrew Aguecheek, and the social climbing Malvolio are thinking that we can't have beautiful, rich, single women running around the play with all that power and wealth. Olivia needs to be married off, ASAP. These guys are all looking to bag Olivia, not because they love her, but because she's a target who seems to have been made just for them to wed and bed. If she can make them rich and/or increase their social status along the way, so much the better. Even Olivia's opportunistic uncle, Sir Toby Belch, is really concerned about whether or not his niece's future marriage will be advantageous for him.
(Tasty inter-textual tidbit: In this way, Olivia's a lot like the heiress, Portia, in The Merchant of Venice. Bassanio initially goes after her for her money and it's really important that she marries a suitable man instead of remaining single, especially since her father is dead. So important, in fact, that Portia's father arranges her marriage from beyond the grave. Want more? You'll have to read about it in Shmoop's The Merchant of Venice analysis. But save that for later because we're not done here.)
The point we're trying to make is that Olivia's status as a potential meal ticket for men places her at the center of the play's concern with the relationship between marriage and social status. (Check out more on this by going to "Society and Class.")
When the play opens, Olivia is in deep mourning for her dead brother. How does she grieve? By cloistering herself like a nun, wearing a black veil, and sloshing her salty tears all over the ground. In the real world (or even a tragedy), we would probably feel sorry for Olivia, but Shakespeare makes it pretty clear that her behavior is just a smidge ridiculous. Not because she won't give Orsino, Aguecheek, or Malvolio the time of day, but because she's locked herself into a very silly lifestyle. In fact, when we first hear about her from Valentine, Olivia's tears are compared to a "brine" that "seasons" her "brother's dead love" (1.1.32, 33). Cue the uncomfortable laughter – Olivia's tears are compared to pickle juice, folks – that's the salty stuff that preserves cucumbers. This makes her something like a pickle-maker, which in turn makes her dead brother something like a pickled cucumber. Pretty gross and pretty absurd, right?
Even Feste the Clown, who we happen to think is the wisest cat in the whole play, goes out of his way to demonstrate the folly of Olivia's behavior when he says that she, not Feste, is the real "fool" for spending all her time mourning instead of living her life. Her somber demeanor is also jarring in contrast to play's festive atmosphere, which is pretty conspicuous in light of the fact that Olivia's house guests (Toby and Aguecheek) party all night while she traipses around her chamber weeping.
OK, Olivia's ridiculous. So what? Critics point out that her excessive mourning is not so different from Duke Orsino's self-absorbed ways. (Remember, Orsino claims that he's in love with Olivia, but we learn that he spends most of his time daydreaming about himself and the idea of love as he wallows around his couch all day.) Olivia, like the Duke, spends all of her time at home instead of engaging with the world around her. She's also preoccupied with her own feelings of grief, which makes her just as self-involved as Orsino. The play's point? Love (when it's directed at living, breathing beings that can reciprocate or want to reciprocate) is great. Being self-involved? Not so much.
Olivia, however, is not completely hopeless. She's sassy, wry, and smart enough to recognize Orsino's ridiculous love messages for what they are – a series of insincere clichés. In fact, Olivia becomes the play's mouthpiece for critiquing the conventions of love poetry when she bags on the Duke's attempts to woo her with the kind of cheesy lines that have been around for centuries.
It seems that Olivia just needs the right person to bring her out of her bad mood. Enter "Cesario," the Duke's boy page who is really a girl, Viola, in disguise. When "Cesario" delivers a message from the Duke, Olivia turns from a pickle-making mourner into an obsessed woman who wants to sink her claws into "Cesario." So, what is it, exactly, that makes Olivia go for "Cesario"? Let's ask Olivia:
Thy tongue, thy face, thy limbs, actions and spirit,
Do give thee fivefold blazon (1.5.297-298)
From the sound of it, Olivia thinks that everything about Cesario is attractive. Let's start with looks. "Cesario's" "face" and "limbs" are so delicious that "he" seems to be a walking, talking "blazon" (a love poem that describes women by comparing them to yummy things in nature – lips like cherries, hair like silk, eyes like stars, and so on).
"Cesario," it seems, is attractive to Olivia because "he's" both masculine and feminine looking. Olivia's also attracted to "Cesario's" "spirit" and "tongue," meaning she likes "Cesario's" saucy demeanor and way with words (Cesario turns out to be quite the love poet). We can see from this passage that Olivia's desire for "Cesario" does some pretty important work in Twelfth Night. In a play that's obsessed with showing us that gender is a slippery concept, Olivia's attraction to "Cesario" demonstrates that androgyny can be attractive. We're also reminded that Olivia acts as the play's built-in barometer for good love poetry – Orsino's scripted verses are lame, but "Cesario's" off-the-cuff musings are sincere and alluring.
Rather than sit around dreaming of sexy "Cesario," Olivia goes after "him." Now seems like a good time to remember that, according to traditional Elizabethan notions of gender, the "ideal" woman is supposed to be silent, chaste, and obedient. Olivia not only breaks out of the stereotypical role she's been assigned to when she proposes to the man she thinks is "Cesario" (Sebastian), but she also breaks from the idea that she should marry a man of the same age and social status when she pursues a young servant. All of this makes Olivia just as unruly and rebellious as figures like Toby Belch and Feste. Her behavior, then, is a significant part of the play's "topsy-turvy" spirit. We don't know about you, but we think this is pretty cool.
OK, we know what you're thinking. Olivia's still pretty silly because she's easily able to transfer all of her passion for "Cesario" into a relationship with Sebastian when she marries Viola's look-alike brother. We admit that this is a little too convenient. But we also happen to think that there's something important to take away from the situation. Olivia's marriage to Sebastian points to the conventions of Shakespearean comedy, a genre that always, always, always ends in marriage and heterosexual couplings as a way to reestablish order in the world. For all of Olivia's unruliness, her marriage to a man ultimately helps to restore order in a chaotic and topsy-turvy world. For all of Olivia's unruliness and unconventional behavior, her marriage to Sebastian helps to reestablish the play's sense of social order. You're thinking this is a total drag, right? Check out "What's Up with the Ending?" if you want to know how Shakespeare resists conforming to social and generic conventions by leaving Viola on stage in her "Cesario" get-up. Trust us. You'll like it.