Chaucer first appears in public records in 1357 as a member of the house of Elizabeth, Countess of Ulster. This was a conventional arrangement in which sons of middle-class households were placed in royal service so that they could obtain a courtly education. Two years later, Chaucer served in the army under Edward III and was captured during an unsuccessful offensive at Reims, although he was later ransomed. Chaucer served under a number of diplomatic missions.
By 1366 Chaucer had married Philippa Pan (daughter of the Flemish Sir Gilles de Roet, called "Paon"--medieval surnames were often changed between generations), who had been in service with the Countess of Ulster. Chaucer married well for his position, for Philippa Chaucer received an annuity from the queen consort of Edward III. Philippa's sister Katherine de Roet (later Lady Swynford, later Duchess of Lancaster) was John of Gaunt's mistress for twenty years before becoming the Duke's wife. Through this connection, John of Gaunt was Chaucer's "kinsman." Chaucer himself secured an annuity as yeoman of the king and was listed as one of the king's esquires.