At nineteen he went with the king on one of the many expeditions of the Hundred Years’ War, and here he saw chivalry and all the pageantry of mediaeval war at the height of their outward splendor.  Taken prisoner at the unsuccessful siege of Rheims, he is said to have been ransomed by money out of the royal purse.  Returning to England, he became after a few years squire of the royal household, the personal attendant and confidant of the king.  It was during this first period that he married a maid of honor to the queen.  This was probably Philippa Roet, sister to the wife of John of Gaunt, the famous Duke of Lancaster.  From numerous whimsical references in his early poems, it has been thought that this marriage into a noble family was not a happy one; but this is purely a matter of supposition or of doubtful inference.

In 1370 Chaucer was sent abroad on the first of those diplomatic missions that were to occupy the greater part of the next fifteen years.  Two years later he made his first official visit to Italy, to arrange a commercial treaty with Genoa, and from this time is noticeable a rapid development in his literary powers and the prominence of Italian literary influences.  During the intervals between his different missions he filled various offices at home, chief of which was Comptroller of Customs at the port of London.  An enormous amount of personal labor was involved; but Chaucer seems to have found time to follow his spirit into the new fields of Italian literature: 

    For whan thy labour doon al is,
    And hast y-maad thy rekeninges,
    In stede of reste and newe thinges,
    Thou gost hoom to thy hous anoon,
    And, also domb as any stoon,
    Thou sittest at another boke
    Til fully daswed is thy loke,
    And livest thus as an hermyte.[71]

In 1386 Chaucer was elected member of Parliament from Kent, and the distinctly English period of his life and work begins.  Though exceedingly busy in public affairs and as receiver of customs, his heart was still with his books, from which only nature could win him: 

    And as for me, though that my wit be lyte,
    On bokes for to rede I me delyte,
    And to hem yeve I feyth and ful credence,
    And in myn herte have hem in reverence
    So hertely, that ther is game noon
    That fro my bokes maketh me to goon,
    But hit be seldom, on the holyday;
    Save, certeynly, whan that the month of May
    Is comen, and that I here the foules singe,
    And that the floures ginnen for to springe—­
    Farwel my book and my devocioun![72]