In Act 1, Scene 1, Fainall describes the "cabal night" (basically a gossip party) where he imagines Mirabell must have been humiliated the night before. Fainall uses a simile and striking imagery to describe the social dynamic at these parties:
[L]ast night was one of their cabal nights; they have ’em three times a week, and meet by turns at one another’s apartments, where they come together like the coroner’s inquest, to sit upon the murdered reputations of the week.
He compares the party to a "coroner's inquest," an official inquiry where a jury helps a coroner determine cause of death. The dead, in this instance, are not people, but reputations. The comparison to a coroner's inquest is supposed to be derisive. Fainall is scoffing at these people (mostly women) for taking their gossip so seriously. At the same time, there is something serious and sinister about what they are doing. The term "cabal" has antisemitic origins. It refers to a group of organized schemers, often coded as Jewish, who try to exert malicious control over society. Antisemitic groups and conspiracy theorists continue to condemn "cabals" (based on false evidence) for trying to take over the world. Fainall uses the term to convey they idea that the gossip nights are not only ridiculous but also poisonous to society.
The idea that the gossipers are gathering around and sitting on already "murdered reputations" adds to the idea that the gossip parties are distasteful by conjuring the image of a group of scavengers, not just jurists. It is easy to imagine the gossipers as a murder of crows, gathering around to pick pieces off reputations that were dead before they got there. Fainall is proud enough of his simile and imagery, horrifying as it is. By giving him this vivid line, Congreve helps the audience see Fainall as a misanthrope who might have some valid critiques about society but who is at least as bad as everyone else.
In Act 1, Scene 5, Fainall uses a simile to describe Witwoud and Sir Wilfull Witwoud in relation to each other:
MIRABELL: Pray, are the follies of this knight-errant and those of the squire his brother anything related?
FAINALL: Not at all; Witwoud grows by the knight, like a medlar grafted on a crab. One will melt in your mouth, and t’other set your teeth on edge; one is all pulp, and the other all core.
MIRABELL: So one will be rotten before he be ripe, and the other will be rotten without ever being ripe at all.
Fainall compares Witwoud to a fruit called a medlar, which is pulpy and soft when eaten. Medlars sound exotic and interesting to many modern readers because they aren't cultivated very often anymore. This is because they were never especially well-liked. Common in England at the time Congreve was writing, they were a frequent symbol in literature for prostitution and promiscuity because the bottoms of the fruits open out. Whereas Witwoud is like this crude fruit, Wilfull is like a crabapple. A crabapple is also not a very well-liked fruit, but that is because it does not soften as it ripens. It is hard and extremely sour when bitten into, and there is not a lot of flesh. It is a bit like eating an apple core.
Mirabell doesn't seem to like either fruit very much—nor would most of Congreve's audience. They represent the least delicious extremes when it comes to fruit: a medlar always tastes rotten, and a crabapple never tastes ripe. The comparison allows Fainall and Mirabell to delineate different types of fools. Witwoud doesn't have much substance and has been made rotten by his participation in London society (for instance, he is regularly included in Lady Wishfort's "cabal" or gossip nights). He moved to London and was corrupted by the rest of the fools he associates with before he could ripen into a more respectable member of society. He is a true "wit would" because he would have been witty if he hadn't first deteriorated into a fool. Wilfull, meanwhile, is far too green to ever make it in London society. His wit is never going to ripen.
The simile furthermore allows the play to comment on nature and nurture. Fainall thinks Witwoud is an altogether different specimen "grafted" onto the family tree. The different lives Witwoud and Wilfull have led have not kept either one of them from being a fool, but they have become different types of fools. It seems that socialization has at least something to do with how people turn out. This view was not brand new, but it was more radical in 1700 than readers today might think. As the middle class expanded and the aristocracy faced more challenges, people were becoming much more invested in the idea that it was possible to move from one social class to another. By describing Wilfull and Witwoud as different types of fools, the play invites the audience to consider the idea of social mobility without totally throwing out the idea of innate characteristics (in their case, heritable foolishness).
In Act 2, Scene 7, Mirabell has a soliloquy after Millamant leaves him alone onstage. He uses an elaborate simile to describe what it is like to be a man in love with a woman:
A fellow that lives in a windmill has not a more whimsical dwelling than the heart of a man that is lodged in a woman. There is no point of the compass to which they cannot turn, and by which they are not turned; and by one as well as another, for motion, not method is their occupation. To know this, and yet continue to be in love, is to be made wise from the dictates of reason, and yet persevere to play the fool by the force of instinct.
Mirabell here reflects on his love for Millamant, describing himself as a "fool" following instinct instead of reason. Like a man who lives inside a windmill, a man in love has no sense of direction and will turn every which way based on the way the wind blows (or, in the case of the man in love, based on the ever-changing mood of the woman he loves). The simile helps the audience see that Mirabell is totally abandoned to his emotions. Millamant has the kind of power over him that the wind has over a windmill. Whereas she has treated their relationship and her rejection of him as a game, Mirabell is extremely sensitive to her comments and will do anything to win her over.
The fact that this speech is a soliloquy (there are no other characters around to deceive) helps the audience see that his love for Millamant is genuine and not performative. The genuine loss of his senses makes Mirabell's scheming and manipulation throughout the play a bit more forgivable (at least to Congreve and his intended audience) than other characters' scheming and manipulation. Mirabell engages in the same duplicity for which Congreve criticizes other characters. What makes him the hero and not another villain is his motivation: he is not seeking control or riches, but rather Millamant's love. In fact, he is so desperate for her love that he loses his otherwise reasonable sense of honor.
In Act 3, Scene 10, Millamant and Marwood develop an elaborate simile-turned-metaphor comparing acquaintances to clothing:
MILLAMANT: Well, ’tis a lamentable thing, I’ll swear, that one has not the liberty of choosing one’s acquaintance as one does one’s clothes. [...] I could consent to wear ’em, if they would wear alike, but fools never wear out – they are such drap-du-Berry things, without one could give ’em to one’s chambermaid after a day or two.
Millamant describes getting tired of acquaintances, and she complains that when she tries to "wear" fools like clothes for a little while, it's hard to get rid of them. She seems to decide partway through that she likes this comparison. She picks up steam and begins using a direct metaphor, simply talking about clothes made out of dull woolen cloth (drap-du-Berry) when she means fools. The only difference between fools and this drab clothing, she says, is that you can't give fools to your maid when you are done with them.
This metaphor is a callback to Millamant's earlier claim that she used love poems from suitors to curl her hair. Millamant prefers to think about suitors as fools rather than wits, and she prefers to think about fools as clothing and accessories rather than real people. This is why she was rather cruel to Mirabell when she broke up with him in Act 2: she simply wants to get rid of him. She can't pass him off to a servant because that wouldn't be an advantageous match for him. There is a bit of a sense here that Millamant worries men want her for her money instead of for herself.
Marwood sees through Millamant's seeming disdain for all the men who have shown an interest in her. She accuses her of "putting on" fools like Petulant and Witwoud (who would be easy for her to "take off") to conceal the fact that Mirabell is sticking to her. Mirabell is the only clothing Millamant can't get rid of, and Marwood wants Millamant to admit already that she likes him.
