Whoever put Pearl first in the Cotton Nero manuscript had good reason for giving it pride of place (if that was indeed the intention). To a reader of the time Pearl must have seemed the most up-to-date and adventurous of the four poems in the book. Technically it is very ambitious, with 101 long stanzas rhymed according to a demanding scheme and linked together by repeated words in groups of five. The poet handles the dreamvision form, fashionable at the time, with great virtuosity, especially in developing the symbolism of pearls. He also brings contemporary theological thought to bear on a private loss – the death of an infant not yet two years old – in an attempt to produce what might be described as a Consolation of Theology. The poem may even owe something to that most advanced of all fourteenth-century vernacular poems (little known in England at the time), Dante's Divine Comedy.

Pearl opens with a curious reversal of the expected relationship between waking experience and dream. In the first group of five stanzas, which form a waking prologue to the ensuing dream, the narrator describes how, one August day, he returned to a grassy place where he had previously dropped and lost a particularly fine pearl, and how at last he fell asleep there. That is what literally happens; but the events acquire a dreamlike strangeness in the telling, as the true source of the narrator's intense distress is enigmatically hinted at. A pearl that rots (l. 26) must be organic; and a pearl with slender, smooth sides (l. 6) sounds, in Middle English poetic language, like a woman; and it is women, not pearls, whose ‘luf-daungere’ (standoffishness or inaccessibility, l. 11) makes men suffer. So is the poem to be a love-allegory? What did the narrator in reality lose? The enigma is left unresolved until, in the dream, the loss is identified as a paternal bereavement. The narrator there encounters his lost pearl as a female ‘nearer to me than aunt or niece’, he says (l. 233), who ‘lived not two years on earth’ (l. 483). These two clues, despite their somewhat evasive phrasing, are enough to settle the matter, when they are taken together. The occasion of the poem, shadowed in its waking prologue, was the death of a one year-old daughter.