The poem is the third longest of Chaucer’s works, after The Canterbury Tales and Troilus and Criseyde and is possibly the first significant work in English to use the iambic pentameter or decasyllabic couplets which he later used throughout the Canterbury Tales. This form of the heroic couplet would become a significant part of English literature no doubt inspired by Chaucer.
The prologue describes how Chaucer is reprimanded by the god of love and his queen, Alceste, for his works—such as Troilus and Criseyde—depicting women in a poor light. Criseyde is made to seem inconstant in love in that earlier work, and Alceste demands a poem of Chaucer extolling the virtues of women and their good deeds.
The poet recounts ten stories of virtuous women in nine sections. The legends are: Cleopatra, Thisbe, Dido, Hypsipyle, Medea, Lucrece, Ariadne, Philomela, Phyllis and Hypermnestra. The work is a similar structure to the later Monk's Tale and like that tale, and many of his other works, seems to be unfinished. Chaucer's sources for the legends include: Virgil's Aeneid, Vincent of Beauvais, Guido delle Colonne's Historia destructionis Troiae, Gaius Julius Hyginus' Fabula and Ovid's Metamorphoses and Heroides.
The incomplete nature of the poem is suggested by Chaucer's Retraction from the Canterbury Tales which calls the work the xxv. Ladies. Fifteen and nineteen are also numbers used to describe the work. In the prologue several women are mentioned—Esther, Penelope, Marcia Catonis (wife of Cato the younger), Lavinia, Polyxena and Laodamia—whose stories are not recorded and the nineteen ladies in waiting of Alceste mentioned in the prologue might suggest an unfulfilled structure.
The command of queen Alceste is said, by John Lydgate in The Fall of Princes, to be a poetic account of an actual request for a poem by Anne of Bohemia who came to England in 1382 to marry Richard II. If true this would make Chaucer an early poet laureate. Joan of Kent, Richard's mother, is also sometimes considered a model for Alceste. The supposed royal command is one suggested reason for the poem's unfinished state as Chaucer got bored with the task and gave up. Several passages hint at Chaucer's dissatisfaction:
Whether the poem's state is due to Chaucer becoming bored with it is uncertain, but it not now regarded among his best work, despite being popular when first written. One early fan is Chaucer's own character the Man of Law who praises Chaucer and the poem which he calls Seintes Legende of Cupide. The work is rather inconsistent in tone, with tragedy mixed rather uncomfortably with comedy and the legends are all rather similar with little of the characterisation which is key to the Canterbury Tales. Some scholars have conjectured that the work is deliberately poorly written and the work is actually a satire against women although this is not widely agreed with. Another idea is that it is a satire on the idea of taking stories of classical origin and twisting them to give them contemporary moral meanings. This would suggest that the poem is not only an early use of heroic couplets but also one of the first mock-heroic works in English.
The nature of the poem with its separate legends makes dating it difficult but it is clearly placed between Troilus and the Tales around 1386/1388. Chaucer seems to have returned to the work a decade later to rewrite the prologue, but the latter text, which survives in only one manuscript, is generally considered inferior to the original.