Class Warfare

Your suggestion, that Malvolio perhaps does not have any romantic feelings for Olivia at all, and that his main aim is to climb the social ladder is interesting. Having a closer look in Malvolio’s reaction after her had read the faked letter hints on his advancing-intentions: “[…]  I will be proud, I will read politic authors, I will baffle Sir / Toby, I will wash off gross acquaintance, I will be point-devise / the very man. […]” (2.5.141-143).
Considering that Twelfth Night also plays with disguise, it may even be possible that he uses having ambitions for Olivia as a mask to conceal his real intentions and plans before the other servants and members of Olivia’s household.

Shakespeare II

I actually pity Malvolio through this point in the play. He is of course thus far cast as the perennial stick in the mud, stymying the good times that his “betters” are looking to have. However it is important to remember his station in life: He is a servant whose life revolves completely around meeting the desires of those who outclass him. It’s not hard to imagine one in that position becoming cold-hearted and intractable.  I do not believe for a second that Malvolio actually has legitimate romantic feelings towards Olivia nor do I think that was Shakespeare’s intention. To Malvolio she is a possible means to an end that prior to finding the faked letter he probably never thought possible: A way out of a life of servitude.

The scene in which Malvolio approaches Olivia in his attempt to woo her contains so much second-hand embarrassment it was painful…

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