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Jay Dougherty compared Prufrock to the character, Guido de Montafeltro, the doomed spirit in Dantes A Divine Comedy. He suggests that Eliot used the headnote from Dante because Guido and Prufrock were both faced with an overwhelming question (Dougherty.) Dougherty goes on to explain that the questions they faced made them question their selves and they way they answered demonstrate the different worlds between them. Pope Boniface VIII who ultimately gives the choice of sin and salvation confronts Guido. The consequence of Guidos sin would be eternal damnation. While the question given to Guido is a clear choice, the one given to Prufrock isnt as clear. Prufrock is also faced with a tough decision, but differs from Guido in his failure to decide. He is plagued by a hundred indecisions and decisions and revisions, which a minute will reverse (lines 32, 48). Dougherty describes this fundamental difference between the two characters, explaining that both Guido and Prufrock are faced with overwhelming questions: both the questions themselves and their responses to them demonstrate the difference not only between Guido and Prufrock but also between the worlds they inhabit (38). Prufrock inhabits an internal, mental sphere where indecision is acceptable, while Guido dwells in a world of external political problems where decision is vital. Dougherty argues that Guido is faced with a clear choice, between helping Boniface and not helping Boniface, between sin and virtue, and hence damnation and salvation, while the question confronting Prufrock is never spelled out, and its source never clearly identified. The poem, rather, focuses on Prufrocks inability, in the absence of any absolute, any right or wrong, to confront the question (39). While both Guido and Prufrock must answer an overwhelming question, Prufrock fails to reply.
Dominic Manganiello affirms in T.S. Eliot and Dante that Eliot connects the situations of the Pilgrim and Guido with Prufrocks both to identify and to counterpoint Prufrocks predicament with theirs.
