Why does Prufrock feel enslaved?
T.S. Eliot's master work is a dramatic monologue that is spoken by
Prufrock (the name is both a pun [on “prudish”] and a parody [of elegant names, such as “J. Alfred”]), a man who feels trapped in the hell of his own inadequacies (hence the epigraph from Dante’s Inferno).
The dramatic situation is that Prufrock, a cultured man going to
an afternoon tea, is consumed with an “overwhelming question” of
whether or not to make a proposition to one of the cultured women
taking “toast and tea” (hence the ironic title “Love Song”). His reluctance, indecision, and fear of rejection dominate lines 1–83. The
“you and I” in line 1 have been variously identified as Prufrock and
a friend, Prufrock and the reader, or Prufrock and himself (perhaps
even Prufrock’s ego and superego or desires and self-consciousness).
The metaphor of evening as an etherized patient (lines 2–3) suggests Prufrock’s difficulty in dealing with his feelings. This is contrasted throughout the poem with the sexual life of the lower classes (“cheap hotels”), almost always linked with water images (“oyster shells”) that suggest sexual activity. The impending visit and the “overwhelming question,” combined with Prufrock’s ongoing impulse to revise, rethink, and retreat, recur as the central motif of the first section of the poem in lines 10–14, 25–31, 46–49, and 79–83. Failure, reticence, and withdrawal—the crisis of the poem—occur in lines 84–86: Prufrock has been “afraid.” Herationalizes and justifies his failure in lines 87–111, assuming that his approach would have been out of place, badly done, misunderstood,and rejected. He imagines that the woman to whom he spoke would have told him that “That is not what I meant at all.”
In the last twenty lines, Prufrock offers an accurate assessment of
his own present and future. The Hamlet metaphor (111–119) identifies him as an insignificant and foolish character, far removed from the vital centers of life. He realizes that life and time have passed him by. The mermaids (sea imagery, sexuality) represent a fulfillment that Prufrock will never have (“I do not think that they will sing to me” —one of the most sorrowful lines in twentieth-century poetry). He can experience such vision in his dreams (126–130), but human voices (reality, society, responsibility) remind him of his failures and his inadequacies. No wonder he feels "enslaved."