Dering, an eminent antiquary, traced his descent from a sheriff of Kent in the reign of King Stephen. The family lived near Lydd until 1430, when they acquired by marriage a manor in Pluckley, renamed Surrenden Dering.
Dering travelled to Calais and Gravelines for a couple of days in August 1620, and two months later set up house at Surrenden. He spent the summer of 1621 in Ireland, where he visited a cousin.
Having gained access to Buckingham’s circle, Dering was now a serious contender for a seat in Parliament. In April 1625 he was recommended to the corporation of Hythe by Sir Norton Knatchbull* of nearby Mersham Hatch as a ‘gentleman in my opinion without exception, religious, learned, stout, and in every way worthy of such a place of trust’. Knatchbull further informed the corporation that Buckingham, who as lord warden of the Cinque Ports had the right to nominate one of the borough’s Members, would ‘without question’ approve of Dering were he to be chosen, as Dering had ‘lately matched in his family’.
Dering supported secretary of state Sir Albertus Morton* in the 1625 Kent county election. Once at Westminster he bought a catalogue of all the names of his fellow Members. He also paid the fees due to the clerk of the Commons and the serjeant-at-arms on 23 June, but played no recorded part in the Westminster sitting. He arrived in Oxford in good time for the resumed session, spending in diet there between 29 July and 15 Aug. the modest sum of £2 15s. He was the first of those given leave on 4 Aug. to come into the House without receiving the sacrament, but left no further trace on its records.
Mindful of the error he had made in not approaching Buckingham for a seat, Dering resolved to speak to the duke in person to request a burgess-ship when a fresh Parliament was summoned at the end of 1625. He made his way to Dover, expecting that the favourite would pass through the port on his way back to London from The Hague, but not finding Buckingham there he wrote to his mother-in-law asking her to intercede on his behalf. However, Elizabeth Ashburnham was not able to speak to her son John until 13 Jan., by which time Buckingham had already sent out his letters of nomination. The duke subsequently assured her that he would have nominated Dering had he known that he wanted a place. Dissatisfied, Elizabeth turned next to Buckingham’s secretaries, Edward Nicholas* and John Packer*, who claimed that Dering might still obtain a seat if one of Buckingham’s clients was double returned. She also approached the lord keeper (Sir Thomas Coventry*), who proved equally unable to help.
Towards the end of 1626 Dering seems to have despaired that his mother-in-law would ever secure him the advancement she had promised. At the very least he decided to take matters into his own hand, for during November he called on Buckingham no less than four times. Further visits followed,
In April 1628 Dering found himself once more a widower. His finances were now in a parlous condition, for although his father had already transferred some of the family estate to him, he was heavily in debt.
In 1629 Dering at last attained the office that he had coveted since 1623. He replaced Hippisley as lieutenant of Dover Castle, having entered into negotiations for the position the previous year.
