Of insidious intent
“Streets that follow like a tedious argument / Of insidious intent / To lead you to an overwhelming question…” These three lines form one simile operating on a couple of different levels.
On a concrete level, we’re given the image of streets that form a sort of labyrinth, a big tangle of paths as confusing as a long argument. “With insidious intent” might mean that these streets lead to bad places (seedy areas of the city, etc.), in which case the speaker is personifying the streets by saying that their confusing layout is designed to lead wanderers to dangerous places.
But “tedious argument” also calls to mind Prufrock’s own internal debate—specifically, as to whether or not to act on his desires with the woman who appears later in the poem. (Or with women in general.) “Insidious intent” might suggest that he’s having this argument with himself in order to “talk himself out of it”: that once he’s faced with the “overwhelming question” of whether to make a move, he will chicken out. It may also suggest that the argument leads to a larger, philosophical despair about his place in the world and his ability to act at all.
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