Prufrock and Sherwood

"The Love Song of J. Alfred Prufrock" by T. S. Eliot and Winesburg, Ohio,  both share the common theme of loneliness. Many of Sherwood's characters find themselves lonely as well as the speaker in "The Love Song of J. Alfred Prufrock." To start, in Winesburg, Ohio by Sherwood Anderson, Wing Biddlebaum is lonely and wants to be with people but is scared to reach out because of his haunting past of being exiled from the town he teaches in. Because of his fear, he stays in his dilapidated house outside of town. He still watches the "berry pickers" (Sherwood 9) with enough space in between them that he doesn't have to converse with them. The speaker in "The Love Song of J. Alfred Prufrock," like Wing, has learned from the past and has "known them all already" (Eliot 49).  The speaker knows that he or she has already been presented with the issue yet he or she has a hard time figuring out how to not make the same mistake again. It also sounds a little sassy to me the way it is said. It's like when a teacher says something in class, and then someone asks about it immediately afterwards. Then the class looks at that person like "Hello? Are you dumb?" In the end, both lonely and wanting to be a part of society.
The two works are different in how the speaker and Alice Hindman thinking about their lives. Alice is "dreaming an impossible dream" (Sherwood 109) which relates to the speaker and his or her wondering and questioning, "And how should I presume?" (Eliot 61). They are both struggling with the fact that they aren't sure where to go. Alice knows what she wants but knows she won't get it. She knows she can't reach it no matter what happens. On the other hand, the speaker doesn't know exactly what he or she should do and is looking for the path to the little bit of happiness he or she can get in the last years of his or her life.
Lastly, in the end of the love song, the speaker says, "Till human voices wake us, and we drown" (Eliot 131). It really reminds me of how the characters in Winesburg, Ohio are grotesque. The grotesques are drowning in other's opinions and mistakes. The other people in Winesburg are influencing certain people as they grow older before they become grotesque. However, it's kind of backwards. I know I'm not supposed to refute myself but I can't decide which side I'm on. In Winesburg, Ohio, the characters are trying to help George Williard by sharing their experiences so he does not become a so called grotesque. However, if he does not experience the mistakes first hand, he cannot learn. That's where I am confused. You are drowning in the voices, yet you are learning. Drowning has bad connotations. When you drown, you typically die. Yet, if we compare it to George Williard, he's learning. But is he learning from the bad in others?? Not sure.