In Joseph P. Lash's 1980 biography, Helen and Teacher, he relates that by 1904, for over a year, John had been asking Anne to marry him. Helen wrote in her 1955 biography Teacher: Anne Sullivan Macy:
I am haunted by a perception that Annie never wholly acquiesced in the fact of her marriage. She gained greater self-control -- she held her darker moods well in hand like an animal trainer, but now and then she could hear them growling, and she said she needed me to keep her quiet and reasonable.
Anne kept finding reasons to refuse John's proposal. Lash offers a variety of explanations. One was Anne's uncertainty about John's ability to handle her fiery nature. Then there was the fact that Macy was a Protestant and she was a Catholic. Although she was not religious, she was uncomfortable about breaking a sacrament by marrying outside Catholicism. There was also the issue of Helen. Although Helen and John had become genuinely fond of one another, Anne's marriage would necessarily alter the relationship between teacher and pupil. The letters that still exist do not reflect any jealousy on Helen's part. On one occasion she exclaimed "Oh, Teacher, if you love John, and let him go, I shall feel like a hideous accident!" If Helen did have any reservations about the marriage she kept them to herself.
John at last overcame Anne's reluctance and they announced their engagement on January 16, 1905. Anne saw her marriage to John as a potential benefit to Helen. She trusted John and felt confident that when she died, John would take good care of Helen. (John was 11 years younger than Anne and nearer to Helen in age. As it turned out, Anne outlived John by four years.)
Prior to her marriage in May 1905, Anne asked her good friend and financial backer Eleanor Hutton for advice:
As the time draws near for me to enter new legal relations, I feel that I ought to make a statement of Helen's and my affairs and suggest a plan for the management of her income in the future. If there is any point that you do not approve, will you kindly tell me how I ought to change it?...
....Of course you know that whatever Helen writes represents my labor as well as hers. The genius is hers, but much of the drudgery is mine. The conditions are such that she could not prepare a paper for publication without my help. The difficulties under which she works are insurmountable. Some one must always be at her side to read to her, to keep her typewriter in order, to read over her manuscript, make corrections and look up words for her, and to do the many things which she would do for herself if she had her sight. I make this statement because Helen's friends have not always understood what the relations between her and me really are. They have thought her earning capacity was independent of me...
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