What is Prufrock's overwhelming question in "The Love Song of J. Alfred Prufrock"?

The “overwhelming question” that Prufrock points to is never explicitly formulated. However, the question invites certain inferences and can be discussed at two different levels. First, the question can be considered in the context of courtship. Throughout the poem, Prufrock makes subtle references to his amorous desires, such as his observation of the “women [who] come and go / Talking of Michelangelo” and the mermaids he sees “singing, each to each.” In all cases, women are figured as desired but distant, and Prufrock’s desires are put under pressure by his feeling that time is advancing: “I grow old … I grow old … / I shall wear the bottoms of my trousers rolled.” In light of this, Prufrock’s “overwhelming question” may refer to a proposal of marriage, a reading that is bolstered by the immediate context in which the phrase arrives for the second time:

And would it have been worth it, after all,

After the cups, the marmalade, the tea,

Among the porcelain, among some talk of you and me . . .

However, the question remains unasked.

The other—and perhaps more important—way to interpret the question is to consider it in a more philosophical or spiritual light. Later in the same passage, Prufrock wonders whether it would “have been worthwhile . . . To have squeezed the universe into a ball / To roll it towards some overwhelming question.” The peculiar image of the universe compacted “into a ball” alludes to Andrew Marvell’s “To His Coy Mistress,” a seventeenth century poem whose speaker, making amorous advances, mentions rolling “all our strength and all / Our sweetness up into one ball.” This allusion certainly bolsters the aforementioned courtly connotations, but the repurposing of a line of love poetry into a metaphysical consideration also points to the tension Eliot creates between the day-to-day world Prufrock inhabits externally and the spiritual doubt he experiences internally. In the end, Prufrock’s question remains unclear, but its scope is grand and its nature is insistent, perhaps touching upon the ultimate meaning of things.

What is the unasked question in "The Love Song of J. Alfred Prufrock"?

Alfred Prufrock is shown to be a master of indecision and procrastination as he heads towards a date with a woman whom he plans to ask "some overwhelming question" once they have finished their afternoon tea:

After the cups, the marmalade, the tea,

Among the porcelain, among some talk of you and me,

Would it have been worth while,

To have bittten off the matter with a smile,

To have squeezed the universe into a ball

To roll it towards some overwhelming question...

Although we are never told what the nature of this question is, we can perhaps infer from the constant indecision and self-doubt and lack of engagement in society expressed by Alfred Prufrock that he is contemplating asking this woman to marry him. However, as much as he longs for romantic love and the courage to assert himself, we see that he is bowed down by an intense fear of being misunderstood and of being ridiculed by others. The poem ends before he reaches his date, and this perhaps suggests that these fears will keep him isolated and alone and he will never come to ask his question.