In 1359 Chaucer was sent abroad in the army of the king and was taken prisoner in France and ransomed in the following year. Prince Lionel (the eldest son of Edward III) himself contributed to the ransom to have Chaucer returned to England. Although it is not known when Chaucer began to write poetry, it is expected that it was around this time.

At the end of his life Chaucer looked back on his career and mentioned the many “songs” and “lays” he wrote, and though we have a number of short poems by Chaucer, few fit this description. It is possible that Chaucer was referring to lost lyrics he wrote on the model of those he would have heard performed in the aristocratic households in which he worked, most (if not all of them) in French. It is therefore possible if not very likely that Chaucer’s first poems were written in French rather than English.  Although we cannot date it with any certainty, not least because it adheres so closely to its source text, it seems likely that Chaucer moved from the writing of such lyrics to translation, since we have a Middle English version of the Romance of the Rose (a 13th-century French poem begun by Guillaume de Lorris and later completed by Jean de Meun), part of which seems likely to have been written by Chaucer. This translation survives in three distinct sections, and it seems likely that Chaucer was responsible for only the first of these, but in those lines, it is possible to see Chaucer developing the poetic vocabulary that made his subsequent writings so distinctive as well as learning a variety of strategies of representation and poetic style.

Chaucer quickly ascended the social ladder governing patronage in aristocratic households, and so, by 1367, he has moved on from ducal households to the royal household, where he must have met and then married Phillipa de Roet, a lady in attendance on Phillipa of Hainault, the queen of England. These royal connections seem also to have launched Chaucer on a more modern sort of working life (giving Chaucer what we might now call a “day job”) as a bureaucrat. That is, in 1374 he was appointed Controller of the Wool Customs, a significant position since wool was the basis of much of England’s wealth in the fourteenth century. He held this position for the next 11 years, during which time the king also sent Chaucer on important missions abroad, missions which appear to have been of a commercial nature, dealing with trade relations. These travels clearly widened Chaucer’s cultural horizons since it is about this time that Italian literature began to figure significantly in his writings, particularly the works of Dante, Petrarch, and Boccaccio. Although we do not know when or how he had the opportunity for such study it is also clear that he learned a great deal in this period about the contemporary sciences, especially astronomy, medicine, physics, and alchemy.

Despite his day job, Chaucer was also extraordinarily productive, and wrote theParlement of Foules, translated Boethius’s Consolatio Philosophiae (a substantial Latin text) and completed two of his more ambitious classicizing texts, Troilus and Criseyde (arguably his magnum opus) and theKnight’s Tale,as well as what later became the Second Nun’s Tale.