I have to agree with #4 and the comment that this poem is a classic that grows with us as we mature and develop. Most people encounter it either in High School or at University, and certainly the universal and timeless themes of angst and anxiety about what others think about us and the way in which indecisiveness can ruin our lives certainly strike a chord in all first-time readers. However, now that I am advancing in years, I find the poem less funny and more terrifying than anything. The fact that Prufrock never makes it to his destination and seems to be trapped in his journey to nowhere seems to create a disturbing analogy to a life that is "measured by coffee spoons" and where old age can only make things worse.
"Prufrock" is one of those examples of great literature that grows as we grow. Every person's context brings a great deal to the reading experience and those readings can and do changes as our own individuals contexts change as we age as well. When I first read the poem in high school, the apprehension of approaching a woman spoke to me as I too was suffering in that regard. Later, when I read it again in college, the essential question, "Do I dare disturb the universe?" grabbed my attention. As I age, the "Do I dare to eat a peach?" echoes some of my own experiences. Great literature speaks to all of us in different ways; Prufrock certainly does that.
When I first read this poem, I was a high school freshman, so I will consider that context as I answer your question.
I think most teenagers can relate to Proofrock's fears of the judgments of others. He describes feeling as if he is "sprawled and wriggling on a pin," and often refers to the things he assumes other people are saying about him. Basically, he's afraid to go to parties and stand out like a big geek. What teenager doesn't relate to that, on some level?
Though it is difficult to relate to a person/character who has reached the end of his life when yours is only beginning, I found ways to identify with Prufrock and understand his self-esteem issues when I was 14. Now, as I get older, I can also understand and relate to his feeling that important moments may have passed him by forever, and that there are things he never got to do in his life that he wishes he could have. So as my context changes, my understanding of the poem changes.
Elliott's "The Love Song of J Alfred Prufrock is a mainstay of English classes introducing the complex world of TS Elliott. Many students will still sympathize, and even empathize, with the poem’s preoccupation with such concerns as loneliness, self-consciousness, fear of the opposite sex, the desire to live meaningfully in a trivializing culture, and pervasive feelings of futility and failure.
These ideas that you see in the poem are greatly enhanced by your own position as you read it. One person who is lonely can see loneliness; one person who is unable to speak to the opposite sex will see another theme, etc.
The poem is greatly shaped by ones perspective. Here it is not enough space to analyze the poem, but you should have a good idea of the perspective of the poem from your own position in life.