Much of this poem is devoted to the first use of the heroic couple by Chaucer to retell in lyrical form the tragic love stories of Cleopatra, Thisbe, Dido, Hypsipyle, Medea, Lucrece, Ariadne, Philomela, Phyllis and Hypermnestra. The primary authors of the primary sources of these stories from which Chaucer makes his own adaptations are Ovid and Boccacio with some pinching from Plutarch and Guido delle Colonne as well. Many of these love stories end with the suicide of the female resulting either from a broken heart at losing their true love or a broken heart at being seduced and abandoned. The overwhelming critical consensus is that taken either individually or collectively, the non-original adaptations of existing tales of tragic love are inferior to the Prologue which sets the stage for why he has chosen to revisit those timeless stories of myth and history.
That Prologue begins by introducing a topic that at the time was a poetic debate of monumental proportions: does one prefer the leaf or the flower? Although professing to excuse himself from involvement this highly contentious argument, ultimately, he comes down fairly obviously within the camp of the cult of the daisy; the daisy being a hardcore thematic symbol of love poetry. That encampment sets the stage for the meat of the Prologue which in turns provides the narrative thrust for the tragic love affairs to follow.
While slumbering, his narrator (presumably Chaucer himself, of course) is visited in a vision by Cupid, the god of love who rebukes him for a career in which he produced so many words that contained so little praise for his female characters. In fact, Cupid goes so far as to accused the narrator of outright heresy when it comes to the recognizing the laws of love and romance. A lifetime of not just creating literature that disparages women, but also translating the works of others that proved equally withering in their low opinion of the female sex has led to these accusations of heretical misuse of his talents from which Cupid can find no path leading forgiveness.
To the rescue arrives Alceste—an ancient Greek princess noteworthy mostly for her unending fidelity to her husband Admetus—with a suggestion for penance on the part of Chaucer. If his career to this point has been one of continual lack of respect not just women, but for the true love that they alone often seem capable of expressing, why not allow the narrator to pursue a path toward forgiveness from Cupid by setting his pen to the paper and repairing the leak in his soul, so to speak. Chaucer sees the wisdom of this penitence and agrees to compose a series of poems that celebrate the profound ability of women to reveal a kind of fidelity that will also be found sorely lacking in the many of the men they have loved.
In this manner, Chaucer not only is given the chance for redemption for his own original creative works, but can find redemption for even his misogynistic translations by choosing as the subjects of his revelatory verse adaptations of love stories already told well by literary giants who preceded him. And thus commences with the series of poems about famous tragic love affairs, starting with Cleopatra’s suicide by serpent following the loss of her beloved Antony.