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5 Louise Bulkley Dillingham: Becoming Miss D a y e a r b e f o r e t h e u n e x p e c t e d d e a t h o f t h e h i g h l y e s teemed Miss Hillard, the youthful Louise Dillingham led Westover chapel services, helped with admissions, taught psychology and advanced French classes, all the while getting to know the students, the teachers, and the nature of the school by “observing and absorbing its life and traditions,” she later wrote. A pupil at the time recalled that she “kept a low profile” and was “very pleasant.” A black-and-white snapshot taken of her at the time shows a sturdy, stocky young woman with a wide generous smile and a very intense gaze, her dark hair combed back in a no-nonsense manner and gathered at the nape of her neck. She was remembered as a firm but kind teacher with a twinkle in her eye, who spoke French so rapidly and in such a soft voice that she was very difficult to understand. She was also an innovative instructor: one of her psychology pupils never forgot that she asked them to create an index for an imaginary psychology textbook. Miss Dillingham observed the school under what she would later describe as “the benevolent guidance” of the other assistant headmistresses, Helen LaMonte and Lucy Pratt, who had been there since the beginning. “In no time she had investigated every nook and cranny from bell tower to underground passage . . . Long before the end of the year she knew us all and every department and we felt she could break the bank of Monte Carlo if she cared to, such confidence and devotion had she roused in every one,” Miss LaMonte remembered. “After Miss Hillard suddenly died, there was Miss Dillingham, a tower of strength and everybody’s friend, ready to carry on 80 ✦ w e s t o v e r with no interruption, ready also to start the changes and growth due to follow.” Five months after the founder’s death, Miss LaMonte wrote to the alumnae that the new headmistress had “great sympathy” with Westover traditions. “I always like to think that Miss Dillingham is Miss Hillard’s choice, a person whom she both admired and loved.” Miss LaMonte was speaking from a point of view that, unfortunately, was not prevalent among the pupils. When Louise Dillingham had arrived as heir apparent, “none of us were too pleased,” recalled a member of the class of 1933. The thirty-six-year-old administrator seemed to the adolescents both older than her years and without the charisma of her predecessor, to whom the seniors dedicated their 1932–33 yearbook. The founder of the school “was an extraordinary woman who really loved the girls, and I never had that feeling about Miss Dillingham,” said another alumna, who graduated in 1934. “It was hard because everybody loved and respected Miss Hillard so much.” The students had also heard that this outsider was going to turn Westover into a college preparatory school, and undoubtedly there was some apprehension about it. And whereas Miss Hillard had melodiously addressed them as, “Now, girls,” the younger headmistress began with a brisk, “Now students,” recalled another pupil, who, nevertheless, liked the unassuming manner of the person she called “Dilly” behind her back. “Miss Dillingham seemed very cold and aloof to us and also very, very academic,” yet another graduate remembered. A few liked nothing about her at all. “She was very shy, and very red, and very fat,” remembered the class president in 1935. It is true that the snapshot of her also shows a young woman with a double chin, piano legs, and an overall fleshiness that made her appear to be without neck, wrists, or ankles. President Franklin D. Roosevelt had been elected a few weeks after she was elected headmistress, and the country was experiencing enormous cultural and political shifts. As capitalism came under attack in the face of widespread unemployment, the appeal of socialism and communism was growing. After the President closed the banks to avoid a panic in 1933, spring vacation was cancelled at Westover because no currency was available to pay for transportation. Nonetheless, Miss Dillingham elaborated upon her educational philosophy with more hope and idealism than she ever would do again. In it, she made the assumption that her young students would be able to...

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