Early Career
After leaving the university he devoted himself to antiquarian studies and to the collection of manuscripts. On 22 January 1619 he was knighted at Newmarket, and in November of the same year married Elizabeth, daughter of Sir Nicholas Tufton. She died on 24 January 1622. According to an entry in his account book, he purchased two copies of William Shakespeare's First Folio on 5 December 1623: this is the earliest recorded retail purchase of this famous book.
Dering subsequently married Anne, daughter of Sir John Ashburnham. Lady Ashburnham, his new mother-in-law, being of the Beaumont family, was a connection of the king's favourite, Buckingham. Through her, Dering strove for court favour and was created a baronet on 1 February 1626 (1627 New Style). Buckingham's assassination in 1628 cut short Dering's ambitions at court. He lost his second wife in the same year that he lost his patron.
On 20 November in the year of his wife's death Dering became one of the many suitors of a rich city widow, Mrs Bennett, and kept a curious journal of his efforts to win her, especially of the bribes which he administered to the lady's servants. Mrs Bennett, however, married Sir Heneage Finch on 16 April 1629, and shortly afterwards Dering married his third wife, Unton, daughter of Sir Ralph Gibbs, his 'ever dear Numps', as he calls her in the letters which he addressed to her. He had lately been appointed lieutenant of Dover Castle, an office for which he paid the late holder of the post, and which brought him in much less than he expected. When he at last managed to be quit of it, he was able to devote himself more freely to the antiquarian pursuits at which he was most at home.
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