Critical readings of T. S. Eliot’s “The Love Song of J. Alfred Prufrock” tend to conceive of Prufrock’s recurring evasion and frustration as deriving from his inability to confess his love, a symptom of the ills of modern civilization. However, this paper reconsiders this prevalent interpretation by intensively examining Dante’s lines from Inferno, which Eliot imports into the epigraph of this poem. Dante’s influence on Eliot have been widely explored already, but most studies investigate only the intertextuality between Canto 27 of Dante’s Inferno, especially Guido’s responses to Dante’s question, with the Prufrock poem. However, this paper pays special attention to Canto 27 of Dante’s Inferno and of Purgatory to show that Canto 27 is the site where Dante comments on human reason. Based on this observation, I argue that Eliot’s poem, by endorsing Dante’s lines, extends Eliot’s criticism of human reason as well. In particular, I understand Eliot’s “individual talent” to be his innovative shift in voice when Prufrock directly addresses the readers as he instantly combines his split self as “we”. This moment of integration overlaps with Dante’s double identification with Guido and with Virgil, transposing Prufrock’s ‘monologue’ within his divided self to an ‘aside’ revealed to the readers. Although the speaker fails his ‘love confession’ per se, we can reassess it to be a ‘great’ confession when Prufrock delivers his shameful story of hesitation directly to the readers in the voice of “we”—where the speaker momentarily oversteps the solid confinement of his excessive self-consciousness.