Toby and Andrew are alike in that they both like to get together and have a good time. Sir Toby is an unrepentant drunkard, and Sir Andrew is a friend who is looking to marry Toby’s niece, Olivia. Both are in love, but the situation is quite different. Andrew wants to cement his fortune by marrying Olivia, and Toby marries a servant, Maria.
Sir Andrew is not very intelligent, and not good with his money. In the conversation between Maria and Toby, it is clear that while Toby is trying to talk up his friend, he is not exactly all he is made out to be.
SIR TOBY BELCH
Why, he has three thousand ducats a year.
MARIA
Ay, but he'll have but a year in all these ducats:
he's a very fool and a prodigal. (Act 1, Scene 3)
Sir Toby, on the other hand, is pretty set. He can mooch off of Olivia without too much trouble. Although Malvolio complains that Toby is about to be expelled at any moment, Olivia is actually pretty tolerant of his carousing. Sir Toby does not need to marry up to be sure to have enough money.
Andrew and Toby are alike in that they enjoy drinking, singing, dancing, and messing around with the fool. The fool understands what they are about, and he does not mind keeping them entertained. Andrew and Toby stay up late singing and drinking, and it irritates Malvolio to no end.
My masters, are you mad? or what are you? Have ye
no wit, manners, nor honesty, but to gabble like
tinkers at this time of night? Do ye make an
alehouse of my lady's house, that ye squeak out your
coziers' catches without any mitigation or remorse
of voice? Is there no respect of place, persons, nor
time in you? (Act 2, Scene 3)
In the end, Toby manipulates Andrew into dueling with Cesario. Andrew is hopeless at that too. He is not the dueling sort, and Cesario certainly is not. Toby and Maria think it is funny. Things turn out pretty well for the two of them, because they get married.
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