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About 1366 he was married to Philippa, dau. of Sir Payne Roet, one of the ladies of the Duchess of Lancaster, whose sister Katharine, widow of Sir Hugh Swynford, became the third wife of John of Gaunt. Previous to this he had apparently been deeply in love with another lady, whose rank probably placed her beyond his reach; his disappointment finding expression in his Compleynt to Pité.
To come to an end of this topic, there seems no possibility of escaping from one of the following alternatives. EITHER the Philippa Chaucer of 1366 was Geoffrey Chaucer's wife, whether or not she was Philippa Roet before marriage, and the lament of 1369 had reference to another lady an assumption to be regretted in the case of a married man, but not out of the range of possibility.
Soon after his return to England, he got an appointment about the Court which brought him a settled income. He now began to think of making himself a home. Among those who followed in the train of Edward's queen, Philippa, when she came to England, were a certain knight of Hainault, called Roet, and his two little daughters. These children were now grown up into very comely young women.
Yet the view was long held, and is still maintained by writers of knowledge and insight, that the Phillipa of 1366 was at that date Chaucer's wife. In or before that year he married, it was said, Philippa Roet, daughter of Sir Paon de Roet of Hainault, Guienne King of Arms, who came to England in Queen Philippa's retinue in 1328.
It was apparently founded on the circumstance that Thomas Chaucer, the supposed son of the poet, quartered the Roet arms with his own. But unfortunately there is no evidence to show that Thomas Chaucer was a son of Geoffrey; and the superstructure must needs vanish with its basis.
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.
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