Having completed his probationary training Trevor started as probation officer in the city of Leicester. There he lived the life of a bachelor, lodging in a bedsit, playing cricket at the weekends and working long hours in his fledgling career. He stayed close to his family often returning to Leighton Buzzard and visiting his sister, Pam, and her new husband Peter. The three of them would spend their summer holidays together.

At the same time, in 1965, a young lady from English heritage decided to leave her native South Africa and explore Europe and her British roots. Diana Clement Gay left her job as an English teacher and obtained a 2 year visa to live and work in the UK. Arriving, to her surprise, to blue skies at Southampton dock little did she know how her life would change. After travelling around Europe with 3 other friends from South Africa, Diana got herself a job teaching English at a school in Slough. In the early summer of 1966, Diana was chatting in the staff room to one of her colleagues who was talking about the holiday he was about to go on with his wife and brother in law to Cornwall. When Diana remarked that she would love to see the place, Cornwall, where her own father had grown up her colleague, Peter, invited her to come along. Pam was livid that Peter had invited a stranger on holiday with them, and made him write a letter of apology to his brother-in-law Trevor. 

No one at the time knew that this holiday would lead to love and be the start of a long and lasting relationship between Trevor and Di.

In late 1966, Trevor's father passed away which was an unexpected shock. However, this event only strengthened Trevor and Diana's relationship. With Diana's visa running out, it was her father who contacted Trevor to indicate that he should 'hurry up and make a decision'. Soon afterwards, at Christmas 1966, Trevor and Diana announced their engagement and plans for a wedding in South Africa took hold.

With the date set, in spring 1967 Diana returned to South Africa. Trevor left the UK on his own in June 1967, flying for the first time via Barcelona and Nairobi to Johannesburg where he was met by Di's brother Nick who was to act as his best man. On 17 June 1967 Trevor and Di were married at the Anglican church of St. Peter and St. Paul in Springs, Diana's home town. The reception took place in her parents' garden. A few days later the newly wedded couple headed to Cape Town, where they embarked on a ship that would slowly bring them back to the UK. Leicester would be their first place of residence as they started their married life.