Sir Toby and Maria are well-matched because they both enjoy life, and they seem to think alike. Sir Toby is above Maria is station, but he does not care. He loves her. She understands him, and there are probably few people who do. She is willing to match his drinking, singing, and carousing. It is a love match.
Olivia and Sebastian are a more unconventional couple. Olivia first falls in love with Sebastian’s twin sister when she thinks Viola is Cesario. Apparently, there are enough similarities between the twins that Olivia’s affections are easily transferred. She thinks she is marrying Cesario at first. Sebastian goes along with the marriage because Olivia is rich and pretty. When he sees his sister, he realizes what has happened.
[To OLIVIA] So comes it, lady, you have been mistook:
But nature to her bias drew in that.
You would have been contracted to a maid;
Nor are you therein, by my life, deceived,
You are betroth'd both to a maid and man. (Act 5, Scene 1)
That leaves Viola and Orsino. Viola loved Orsino from the beginning, but she could not tell him because she was pretending to be Ceasrio, and apparently Orsino never noticed she was not a boy. At the same time, he came to appreciate Cesario/Viola’s wit, and even though he used her to woo Olivia he seemed to enjoy her company. Viola, for her part, wished she could just tell him the truth. She tells him, in a way, pretending to describe her sister.
A blank, my lord. She never told her love,
But let concealment, like a worm i' the bud,
Feed on her damask cheek: she pined in thought,
And with a green and yellow melancholy
She sat like patience on a monument,
Smiling at grief. Was not this love indeed? (Act 2, Scene 4)
The matches that do not work out are with Olivia, and they are all one-sided and superficial. Toby's friend Sir Andrew wants to marry her just because she is wealthy. She barely knows he is alive. Malvolio also wants to marry her, but she thinks of him as a servant. Maria, Andrew, and Toby trick him into thinking she returns his affections. Orsino seems to be infatuated with Olivia, but again barely knows her. The least superficial of the failed matches is Olivia and Cesario. She likes "him" for his wit. She falls in love with him despite herself, actually. He reminds her what it is like to feel again, since she has been locking herself away in mourning.
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