wrote a worried letter to her sister saying that her only child was no longer lighthearted. In her reply, Mary said that at school Phyllis was “bubbling over with interests and fun,” and that it was a “tremendous” transition to go from school to home in the summer. She also elaborated on her theory about female development, writing that the maturity of girls depended on “shattering their self consciousness” by using their minds. In her letter, she wrote that Phyllis should think “how someone she dislikes would act in [a] situation—for she is free of self in thinking of someone she dislikes and how she would act. It is all a matter of using one’s brains and recollecting how little other people are ever thinking of those about them—any more than we are thinking of those about us”. She reassured her sister that it was natural for teenagers to be moody and melancholy, and she predicted that Phyllis would go through many other stages. All adults can do is to create wholesome conditions for them, her aunt wrote, and then “let them grow! Mother Nature is wiser than we are. Leave it to her. The flower too goes through many phases before arriving at bloom and fruitage.” She added: “If you could hear how every mother with her first daughter is astounded, dismayed, perplexed and discouraged you would take comfort.”
A year and a half later, Phyllis’s aunt decided that her niece was ready for a glamorous evening gown and a more sophisticated social life. “Aunt Mary has given me a new party dress!!!!!” Phyllis wrote to her mother. “It is a heavenly shade of blue with silver on it. It is rather of a turquoise blue and is chiffon with ends floating from it all around!!!” The aunt and niece then planned to go together to New York City to a Westover friend’s debutante dance at the Metropolitan Club. “Aunt Mary said she didn’t know whether I would have a good time, but it would add to my experience anyway,” the girl confessed to her mother.
Miss Hillard also freely gave advice to other parents about how to bring up their daughters. In a letter to the father of young Betty Choate, she first praised the girl’s personality, but then politely stated that she was immature and needed to spend a year in Europe. The headmistress also bluntly said that he and his wife should spend more time with their daughter. Many times, in fact, she advised parents to become less distant dominating figures and be better friends with their children. Speaking of all young people, she rhetorically posed a question to parents on Visitor’s Day in 1923: “How can you help them?” And then she gave the answer: “Give up authority—that was only to protect them. Substitute companionship,” she said, and “enter into their troubles and their ambitions.”
Girls encircling the West apple tree inside the Quad. WESTOVER SCHOOL ARCHIVE.
While the principal preached to parents, she also scolded pupils from time to time. She was strict about decorum, especially in the dining room, and girls rarely tried to defend themselves. When a spider dropped down the front of a new girl’s dress during dinner one time, she let out a cry. Everyone in the dining room became silent, and Miss Hillard told her to go to her sitting room after dinner, where the girl was informed about the time a mouse ran up another girl’s leg in chapel, but she remained silent and held onto it until the service was over. When the headmistress was dismayed by what she perceived as a diminishment in the spirit of the school, she would start what were called “reigns of terror” that lasted for days. In February of 1912, for instance, she went to the schoolroom “with trouble written all over her face” to talk about a prank the day before, when girls had dressed up a dummy in a uniform to fool a new teacher. Miss Hillard told the assembled school that the joke had, in the words of a student, “hurt her pride in the girls so [much] that she kept from breaking down before us only with the most heroic effort,” Jessica Baylis wrote to her parents. Then the headmistress asked those involved to stand up, and when they did, she spoke to them sternly.
A troubling aspect of Miss Hillard’s personality was her tendency to favor some girls over others. She evidently liked leaders and well-rounded students, partly because they were excellent examples to others. She begged the mother of Rachel Latta to send her daughter back to Westover after a year abroad, and when she did, Miss Hillard wrote that “I am glad for Rachel, and deeply glad for the school.” Rachel had impressed the principal during her sophomore year, and as a senior she fulfilled her promise and was named by the other pupils as the most studious and athletic student and the second best all-around girl in the school. She and another girl were also ranked the most attractive. Miss Hillard’s favoritism had its limits, however. Even though Rachel was a favorite, she lost her good conduct medal after sitting in front of the fireplace in the Common Room for an hour one night after lights out.
Although girls were not allowed to go away on weekends until senior year, when Theodate Pope Riddle invited her younger twin cousins for a weekend at Hill-Stead, Miss Hillard let them go, explaining that she was granting the favor to Mrs. Riddle, not to the girls. In another case, when Margaret Bush was a new girl and asked her headmistress if she could change roommates, she replied, “Margaret, I have never made a mistake in the kind of a girl I’ve admitted to Westover, but I see that I have made one in you.” Margaret felt crushed, but when the term was over Miss Hillard changed her mind and let her do it. (She declined.) The young woman turned out to be a leader who was elected president of the senior class, but in her opinion she and her sister were given special privileges only because their headmistress was so fond of their father. “Not everyone liked Miss Hillard because she had favorites,” admitted another student. “I liked her because I was one of her favorites.”
Although Mary Hillard knew that it was often difficult “for a girl to leave home and learn to stand on her feet,” as she put it to her sister Emily, she was not always sympathetic toward homesickness. “The shock and surprise and excitement of it often make a young girl really ill even though she may be really enjoying it,” she theorized. This attitude is evident in the case of Jeannette Rich, who spent most of her first months at Westover in the infirmary suffering from psychosomatic aliments caused by extreme homesickness. One day when she saw Miss Hillard in the hallway on her way to New York, she timidly asked if she could go home a few days early for Christmas vacation. The headmistress snapped at the girl that she could go home and stay home because she was physically, mentally, and morally weak. The girl burst into tears and rushed off to find Helen LaMonte, who comforted her throughout the rest of the day, until Miss Hillard telephoned and softened her harsh words. Later that year, when Jeannette was in the infirmary with a sports injury, the headmistress stopped in to see her, remarking that she was glad for the accident because it gave the girl a chance “to exercise fortitude.” Although shocked by her words at the time, Jeannette never forgot them and afterward even found them helpful.
While Miss Hillard’s discipline was often erratic, either too strict or too permissive, it was sometimes relieved by her sense of humor. In the late 1920s, she used to board the bus of girls going to Taft for a tea dance to make sure no one was wearing lipstick or rouge. Once when she ordered a pink-cheeked blonde to rub the rouge off her face, the petrified girl denied that she that she was wearing any. The headmistress, the girl remembered, “stared at me for a breathless second, and then with that twinkle that occasionally appeared, she said, ‘My dear, I congratulate you.’” Another time when a student took a dare to sleep in the headmistress’s bed when she was away and was discovered upon her early return, Miss Hillard was again amused.
Her way with girls, however, did not work as well with boys, at least with her nephew, Archibald MacLeish, a son of her sister Martha. When, at Mary’s urging, Archie was sent from his home near Chicago to Hotchkiss School, a boys’ preparatory school about forty miles from Middlebury, she became as close to him as she had been to her deceased younger brother John. “I have a new young nephew come East to school,” she wrote happily to a friend. “He spent Sunday with me and kept me inwardly smiling [because] he was so dear and unconscious and so funny.” That autumn her youngest nephews were christened in Westover’s chapel with Archie and a cousin acting as godfathers and Aunt Mary as godmother. The moving service, attended by relatives, friends, students, and staff (including the handyman, maids from the
