The usual phrase is “tall, dark, and handsome”, but the “Five Foot Assassin” is only 5' 3" so he puts his own spin on it.

As Phife puts it in ATCQ’s “Stir it Up” he’s “the height of Muggsy Bogues…”

…complexion of a hockey puck."

Do you think you’ll miss your calling or that life will never present you with the opportunity to fulfill a dream? Are you a man or woman who feels that—irrespective of how smart or rich or tough you are—no one could ever love you? If so, then you know how Prufrock feels. Poor poor Prufie.

These “mermaids” are a likely reference to the sirens in Homer’s Odyssey. The sirens sang beautiful songs to distract sailors and ultimately lure them to their demise. Prufrock believes himself so undesirable that not even those (fictional) women would call to him. He is also using mermaids here as a metaphorical stand-in for the elusiveness of beautiful women in general.

Would it have been worth it to make a move and risk social shame? The existential ‘overwhelming question’ is never specified. The reader can make any interpretation, but the momentous search by Prufrock for some sort of authenticity and self-determination, some action that will propel him out of the stifling social prison, fails — as later in the stanza we see that he doesn’t even attempt it.

Note the hyperbole of lines six and seven, the reference to the ‘universe into a ball’ and the ‘overwhelming question’, which are designed to leave the reader speculating as to what possible action Prufrock could take. The reference to Lazarus that follows leaves us, deliberately, no clearer.

Note the ironic intertextual allusion to Andrew Marvell’s poem “To His Coy Mistress,” the most famous carpe-diem, poem in the English language:

Let us roll all our strength, and all
Our sweetness, up into one ball;
And tear our pleasures with rough strife
Through the iron gates of life…

The seduction attempt of Andrew Marvell’s poem is ironic; it fails to help Prufrock.

Works and Days is a didactic poem of 800 verses written by the ancient Greek poet Hesiod around 700 BC.

Works and Days chronicles the experiences of Hesiod’s daily life and work, and – laced with episodes of fable, allegory, and personal history – forms a sort of Boeotian shepherd’s calendar.

This could connect with the shepherd reference from Marvell in the first line of the section, perhaps contrasting the simplicity and physicality of the pastoral life with Prufrock’s own inward, frustrated urban life.