This can certainly be a challenging poem to understand at first reading. However, key to understanding this poem is recognising that Alfred Prufrock is a man who is considering asking a question. This question haunts him, but he cannot force himself to utter the words needed to ask it. We can infer that this question is a proposal of marriage to a woman that he is on his way to meet while walking through the city. He is a man who is preoccupied and concerned about his personal appearance. He feels confident that he is well dressed, but expresses concern about the thinness of his arms and legs and his bald patch:
Time to turn back and descent the stair,
With a bald spot in the middle of my hair--
(They will say: "How his hair is growing thin!")
My morning coat, my collar mounting firmly to the chin,
My necktie rich and modest, but asserted by a simple pin--
(They will say: "But how his arms and legs are thin!")
He is thus a characted who is dogged profoundly by self-doubt and a lack of self-confidence. He intensely desires to have the courage necessary to assert himself and is a character that longs for love, yet he is also constantly in fear of others making fun of him or being misunderstood. This fact makes real connection with others impossible. In the end he is forced to concede that his natural timidity and lack of confidence, combined with his fear of failure will prevent him from achieving his goals and gaining a meaningful relationship.