Drake's father, Rodney Shuttleworth Drake (1908-1988), had moved to Rangoon, Burma, in the early 1930s to work as an engineer with the Bombay Burmah Trading Corporation. There, in 1934, his father met the daughter of a senior member of the Indian Civil Service, Mary Lloyd (1916-1993), known to her family as "Molly". Rodney Drake proposed to her in 1936, though they had to wait a year until she turned 21 before her family allowed them to marry. In 1950 they returned to England to live in Warwickshire at their home, "Far Leys", in Tanworth-in-Arden, south of Birmingham, the city where Rodney Drake worked from 1952 as the Chairman and Managing Director of Wolseley Engineering.

On returning to England, Drake moved into his sister's flat in Hampstead, London, before enrolling at Fitzwilliam College, Cambridge University that October to study English Literature. His tutors found him to be a bright student, but unenthusiastic and unwilling to apply himself. His biographer, Trevor Dann, notes that he had difficulty connecting with staff and fellow students alike, and points out that official matriculation photographs from this time reveal a sullen young man. Cambridge placed much emphasis on its rugby and cricket teams, yet by this time Drake had lost interest in playing sport, preferring to stay in his college room smoking cannabis, and listening to and playing music. According to fellow student (now psychiatrist) Brian Wells: "they were the rugger buggers and we were the cool people smoking dope."  In September 1967, he met Robert Kirby, a music student who went on to orchestrate many of the string and woodwind arrangements for Drake's first two albums. By this time, Drake had discovered the British and American folk music scenes, and was influenced by performers such as Bob Dylan, Donovan, Van Morrison, Josh White and Phil Ochs. He began performing in local clubs and coffee houses around London, and in February 1968, while playing support to Country Joe and the Fish at the Roundhouse in Camden Town, made an impression on Ashley Hutchings, bass player with Fairport Convention. Hutchings recalls being impressed by Drake's skill as a guitarist, but even more so by "the image. He looked like a star. He looked wonderful, he seemed to be 7 ft [tall]."  Hutchings introduced Drake to the 25-year-old American producer Joe Boyd, owner of the production and management company Witchseason Productions. The company was, at the time, licensed to Island Records, and Boyd, the man who had discovered Fairport Convention and been responsible for introducing John Martyn and The Incredible String Band to a mainstream audience, was a significant and respected figure on the UK folk scene. He and Drake formed an immediate bond, and the producer acted as a mentor to Drake throughout his career. A four-track demo, recorded in Drake's college room in the spring of 1968, led Boyd to offer a management, publishing, and production contract to the 20-year-old, and to initiate work on a debut album. According to Boyd:  In those days you didn't have cassettes--he brought a reel-to-reel tape [to me] that he'd done at home. Half way through the first song, I felt this was pretty special. And I called him up, and he came back in, and we talked, and I just said, "I'd like to make a record." He stammered, "Oh, well, yeah. Okay." Nick was a man of few words.  In a 2004 interview, Drake's friend Paul Wheeler remembered the excitement caused by his seeming big break, and recalled that the singer had already decided not to complete his third year at Cambridge.

How did he meet her?
February 1968, while playing support to Country Joe and the Fish at the Roundhouse in Camden Town, made an impression on Ashley Hutchings,