Ernest Shepherd was born in 1871. His mother died soon after he was born and then his father committed suicide. Ernest and his brother, Fritz, and his two sisters, Gertrude and Daisy, were brought up by his mother's unmarried sister, Zoë Sinclair.
The family lived at 3 Warwick Square, London. Ernest was educated at Clifton College where he became friends with Henry Mayor, the son of Reverand Joseph Bickersteth Mayor and Alexandrina Jessie. In time, Henry introduced Ernest to Flora Mayor.
Shepherd became an architect. He also had a strong interest in music and art. Sybil Oldfield, the author of Spinsters of this Parish (1984), pointed out: "Ernest Shepherd was a tall, thin, very gentleman-like man, with a kind, humorous brown eyes hidden behind glasses, a drooping moustache and an immense capacity for caring about other people's feelings."
Flora Mayor introduced Shepherd to Mary Sheepshanks. As a result he volunteered to teach students at her Morley College for Working Men and Women. Shepherd was a great success at the college: "His enthusiasm for church architecture and for conducting student excursions to local landmarks - in fact for every kind of antiquity - was infectious."
On 23rd June, 1900, Shepherd, Flora Mayor, Mary Sheepshanks and Frank Earp went to Queensgate House together. Flora wrote in her diary: "Mary Sheepshanks came to lunch looking very pretty. We met Ernest and Frank Earp and went on the river, most successful and most cheerful tea. Ernest was very lively, possibly owing to Mary. Mary talked a good deal about Mr. Fountain's engagement."
Ernest Shepherd became very fond of Flora Mayor, who at that time was working on her first novel, Mrs Hammond's Children. She showed the manuscript to Shepherd. He praised it and encouraged her to send it to a publisher. Flora's novel was nearly completed when she was employed by the Benson Shakespearian Company at the Lyric Theatre, in December 1900. Flora received no pay for the first six weeks, then 15 shillings a week thereafter. Over the next few months she had small parts in The Taming of the Shrew and The Merchant of Venice. Flora was disturbed by the behaviour of some male members of the company. She wrote in her diary: "There is a great deal more pawing and squeezing from the managers than one is used to."
Ernest Shepherd came to see her in the plays. She wrote in her diary: "Ernest was so very nice. He is such a good friend, so awfully sympathetic. He said several times how lucky Benson was to have me." However, when the season came to an end, Flora was not retained. Flora Mayor returned to her novel writing. When it was finished she sent it to a publisher. It was rejected as not "being suitable neither for children nor for adults". Other publishers took a similar view but it was eventually accepted by a small firm called Johnson. Mrs Hammond's Children was brought out in September 1901 but it was ignored by the reviewers and sold very few copies.
Shepherd had fallen in love with Flora Mayor but he was not earning enough money as an architect to marry her. In March 1903, Ernest took a well-paying post as part of the Architectural Survey of India. He then proposed to Flora. At first she hesitated because she did not want to be separated from her family. She wrote to her twin sister, Alice: "I don't like the thought of India... what am I to do without you?" Flora also suspected that Ernest was really in love with Mary Sheepshanks. This he denied and eventually she agreed to marry him.
Under instructions from Flora, Shepherd went to see Mary. That night he wrote to Flora: "I called on Mary Sheepshanks today and told her about ourselves; you know I said I should... Of course I did not expect her to care one way or the other and I don't think she did; but she spoke very nicely, and was pleased that I had come to tell her; so though it was very awkward, embarrassing and hateful I am very glad I did it."
In April 1903, Shepherd left for India and Flora Mayor agreed to travel to the country to get married later that year. He wrote to Flora on 11th July complaining about his colleagues: "The men are unutterably dull - they never talk of anything but sport and bridge; and are intensely competitive about tennis... I don't know anybody - never shall know anybody as far as I can see; everyone is so exceedingly reserved." However, he did grow to love the country. On 2nd August he wrote: "I believe I am getting to like India - The lovely bright sun and clear air, the beautiful views of the country through the arches of the mosque quadrangle." In their letters they made arrangements to get married in Bombay.
In October, 1903, Ernest Shepherd was taken ill and he was sent to hospital in Simla. He wrote to Flora on 7th of that month: "Don't be alarmed at this address... When I went to see the Doctor on Monday he said I wasn't getting on a bit and looked the picture of misery - which I thought a gross libel - and therefore I'd better go into hospital and take vigorous measures to get well, which seemed sensible."
Ernest Shepherd died on 22nd October, 1903. He had been suffering not only from malaria but also from an undiagnosed acute enteric disorder. Flora later recalled that the telegram said: "Deeply regret Mr Shepherd died yesterday, funeral today." In her diary she wrote: "I read it over and over but it really didn't convey anything."
A few days later Flora Mayor received a letter from Fanny Fawcett, the woman who nursed him in Simla, enclosing a lock of Ernest's hair: "He (Ernest Shepherd) was conscious up to the last, but very, very weak of course. Just at the end I asked him if he had any message for you, and he said Tell her I have never forgotten her, and his last words were Best Beloved. I send you some of his hair which we cut off for you. He looked so peaceful and he was taken to his last resting-place surrounded by friends and exquisite flowers. Forgive a complete stranger saying so, but oh! his love for you was so true and ever-present with him, and I want you to feel this and to know his last thoughts were yours."
Flora kept a grief journal where she carried out a conversation with Ernest. The final entry was nine years later: "It is just ten years ago since our engagement. I am forty. You seem so young, thirty-one. I always love best your letter to Alice and the one about Alice to me. Help me if you can to cure my faults and make me more tender, you are so much much more unselfish. Each year brings us nearer."