The poem is not a Browningesque dramatic monologue, but rather an internal monologue in which "I" (the timid self) addresses his own amorous self as "you." Can the "you" also mean the reader, or us?
How does the speaker's name help to characterize him ("Prufrock" suggests "Prude" and "frock")? What suggestions --of class, race, personality--do you find in the name? What is the story in the poem? Considering the story, does the poem's title strike you as ironic?
What qualities of the city life are suggested in the poem? How are these qualities linked to the speaker's mood?
What kind of society is presented in this poem? What ideologies do you find represented by this society, Prufrock and then the poet himself?