In the spring of 1915, Theodate impulsively sailed to England on the luxurious Lusitania for a meeting of the Psychical Research Society in London, despite warnings about German submarines. After it was reported that the passenger ship had been torpedoed and quickly gone down, Mary rushed to Mrs. Pope’s side in New York as they anxiously awaited word of Theo’s fate. As Theo clung to an oar and thought she was going to drown, she counted the buildings she had designed, she later wrote to her mother. After hours in the ocean, she was pulled out and left for dead before someone noticed her eyelids flickering. Almost a year to the day after her rescue, Theodate’s Holiday had to be renamed Mrs. Riddle’s Holiday, after suddenly, at the age of forty-nine, she married John W. Riddle, a tall, thin American diplomat with a large handlebar mustache. Mary slyly suggested in a letter to a sister that it was fortunate that Mr. Riddle had a lot of diplomatic experience. Still, Theo’s former teacher was one of the few guests invited to the small wedding in Farmington, where the bride wore pale blue and carried a silver-tipped walking stick. She soon fulfilled her girlhood dream about raising orphaned children in the country.
While Theo was trying to adjust to married life, Mary was attempting to perfect her community of girls and women. She was well aware that in any group a hierarchy develops, particularly among young girls. Some liked each other too little, the headmistress thought, and others liked each other too much. Pupils were often warned about the problems. In the May 1920 issue of The Lantern, an editor cautioned classmates about finding fault with each other. “We are terribly critical here, of each other, and we have no right to be. If anyone outside of the school asked you what the girls of Westover were like, you’d have the nicest things possible to say, and they’d be perfectly true. Why, then, when we’re here together do we let criticism play so large a part in conversation?” The following year the December issue addressed the problem of exclusionary cliques. “It is always natural that one should see more of certain people than of others … But does no one feel that at times we let ourselves become so intimate with a certain group of girls, that we lose entire sight of many others? … The result proves to be that we are often, perhaps unconsciously, hard, hasty, and unkind.”
Miss Hillard discouraged cliquishness by encouraging girls to follow their interests in school publications and in dramatic, language, and other clubs. “She wanted everyone to be friends with everyone else,” a pupil recalled. When a group of ten or so girls formed a secret society in the 1920s, they knew that if the headmistress found out, she would be furious and forbid it. It was also assumed that she would look unkindly on requests to change roommates. The influence of cliques varied from class to class, of course, but it was an excellent sign that pupils were mindful of the attitude against them and addressed the issue openly. So is the fact that some graduates remember no unfriendliness at all. “I can remember little meanness and no cruelty,” recalled a student long after graduation, only “a simple, generous, and harmonious atmosphere.” Certainly Mary Hillard had a high regard for friendship. As she had written to Augustus Jaccaci, friendship is “much deeper than [the] exchange of thought, that is part of it, and a beautiful and stimulating part, but exchange of sympathies, and of courage, and of comfort may all be silent yet how tremendous is the difference it makes to have them. Such exchange is nothing short of spiritual.”
While she encouraged female friendships, she was wary of what she called “exaggerated friendship.” This was one of the topics that she talked to her girls about. In the December 1911 issue of The Lantern, an editor mentioned that “Miss Hillard’s annual talk on crushes came the other day,” but she did not elaborate on what the headmistress had said. When “crush” became a forbidden word, girls used other words like “want” and “tra-la” for it. Nevertheless, the adolescents exchanged valentines and flowers, made dates for going to chapel and concerts together, and slept in each other’s rooms and even in their beds. Younger girls who idolized older ones would go into a senior’s bedroom in the morning to shut her window or make her bed. This was natural and appears to have been much more emotional than erotic. Jessica Baylis confided to her diary that she had a crush on a senior named Polly, and she carefully kept count of the number of times—eight—that she had slept in her room. In her case, it was innocent enough: “I can safely say that I never learned to love any girl so much in so short a time. The most I did was to tell her that she was a dear and give her a bear hug.”
Such infatuations are commonplace in an isolated and sequestered female community. Besides being way out in the country, Westover was surrounded by a seven-foot fieldstone wall. Within the school, it was forbidden to read newspapers that reported scandals. In this atmosphere, Miss Hillard gave sensible advice about health: she warned girls about smoking, too much dieting, and about drinking more than one cocktail at a time. Other more benign behavior was under scrutiny. Besides being marked on room tidiness, girls were graded for their posture. If someone yearned to be alone for a while, she could place a sacrosanct sign that read “Please Excuse” on her bedroom door or on a pile of books asking respect for her privacy or possessions. The cure for low spirits was considered to be going on a long walk or doing something for someone else.
An outsider’s eye offers another perspective, so it is fascinating to read the description of a visit to Westover in February of 1925 by a Russian political exile named Vladimir Zenzinoff. Mary Hillard had an intense interest in the Russian Revolution, and she invited him to Middlebury to give a talk. Undoubtedly eager for the generous lecture fee, he agreed and was met at the Waterbury train station by a teacher and driver in a luxurious automobile with a fur throw. They drove over the snowy, wooded, hilly landscape to the three-and-a-half-story school, which Zenzinoff described as “an enormous and elegant stone house.” Middlebury in winter vividly reminded him of his village in Russia, and his descriptions are reminiscent of Charlotte Perkins Gilman’s imaginary Herland, too. “It seemed to me as if I were in a fairy tale,” he remembered, and his three days at Westover would turn out to be “unquestionably … the most pleasant, cheerful days [and] the most interesting” of his four months in America. His guest room “had a distinctly maidenish atmosphere about it … purity, immaculateness, a naive simplicity [with a] … snow-white, comfortable bed near the window.” But in some ways—the electricity everywhere and telephone in his room—the school did not remind him of his native land at all.
After being told that dinner would be in half an hour, the visitor, who spoke French but little English, admitted to himself that “still I did not know what sort of a school it was, where I was, nor who would compose my audience.” A group of teachers met him in the small dining room along with Mary Hillard, “who in her majestic bearing reminded one of Catharine the Great.” Through the door to the adjoining main dining hall, he heard the sound of “gay” young voices and tried to look inside, but all he could see were “rapidly moving white silhouettes.” Then he understood. “It appeared that I was in a school for—girls! Fear seized me, but soon this gave way to the courage of despair!” After dinner Miss Hillard led him to her sitting room, which was softly lit and warmed by a fire. He noticed a Russian samovar, which had been electrified to boil water more quickly. There were bookcases and upholstered furniture, as well as a piano and a large round table covered with books and magazines. “Seldom had I seen surroundings more comfortable, more attractive, more cultivated,” he wrote in his memoir.
Soon his hostess was called away, and Zenzinoff realized that what he called an “enormous, magnificent” room—Red Hall—was filling up. “Girls’ voices coupled with laughter became more and more audible, then suddenly silence reigned and I heard Miss Hillard’s voice.” She entered the sitting room where he waited and asked him to follow her, which he did with trepidation. In the big room “broad rows of chairs [were] densely covered with white figures,” he remembered. “On this white background only the faces