Chapter 1: An Ugly Duckling
- ashleywaller0830
- Sep 25
- 3 min read

Anna Eleanor Roosevelt was born October 11, 1884 in New York, New York. Eleanor’s mother, as she put it in her autobiography: “…belonged to that New York City society which thought itself all-important.” (Roosevelt, 4) Her father, Elliott, was a younger brother of Theodore Roosevelt; Eleanor described him as “…charming, good looking, loved by all who came in contact with him, had a background and upbringing which were alien to my mother’s pattern.” (Roosevelt, 4); (I guess you could say opposites attract) Eleanor had two younger brothers: Elliott Jr and Hall (given name Gracie).
Eleanor described herself as a “…shy, solemn child even at the age of two…” (Roosevelt, 5) Her father was the love of her life in childhood, however his struggles with alcohol began around this time (something I can relate to), which she later attributed to pain resulting from a broken leg he sustained that had to be broken and reset. Her mother, however, was a different story: Eleanor states in her memoir that “My mother was troubled by my lack of beauty, and I knew it as a child…” (Roosevelt, 6) Eleanor also disclosed that her mother’s nickname for her was Granny due to her being old-fashioned (“I wanted to sink through the floor in shame”) Her mother’s projected disappointment would lead to a life-long struggle with self-esteem. (something else I can relate to) Even while coming to terms with this adversity, Eleanor was learning about giving back to the community; in her memoir, she describes experiences with both sides of her family in which she has served meals to the poor and dressed Christmas trees for sickly children. It was highly unusual for wealthy families to partake in charity endeavors, as many believed they were above helping those less fortunate. This set the foundation for Eleanor’s empathy with the common man (and woman!)
Eleanor’s difficulty feeling comfortable in her own skin was just the beginning of a trying childhood; shortly after her eighth birthday, her mother would die from diphtheria, a bacterial infection (antibiotics did not exist at this time). From her memoir: “I can remember standing by a window when Cousin Susie told me that my mother was dead… Death meant nothing to me, and one fact wiped out everything else. My father was back and I would see him soon.” (Roosevelt, 9) It is clear that Eleanor’s reaction to her mother’s passing was mixed. As she later learned how hard her mother’s death hit her father, she created a fantasy in her mind that she would travel the world with him and eventually make a home for him to live in with her and her family. (something children tend to utilize as an escape from emotional pain) Not even six months later, her younger brother Elliott Jr. would also die from diphtheria. However the worst tragedy that could happen to Eleanor as a child occurred in August 1894 when she learned that her father had passed away; from her memoir: “My aunts told me, but I simply refused to believe it, and while I wept long and went to bed still weeping I finally went to sleep and began the next day living in my dreamworld as usual.” (Roosevelt, 13) Again, she continues to utilize her fantasy world as an escape from her emotional pain.
In autumn 1899, Eleanor traveled with her Aunt Tissie to England to be enrolled in a boarding school called Allenswood just outside London. It was always her mother’s desire to send her to Europe for a part of her education. (must have been nice to have been wealthy) While she admitted in her memoir that she felt lonely when she was left at Allenswood, another aunt had previously been taught by the French headmistress Madame Souvestre at a school in Paris, so her family felt more comfortable sending her to an institution familiar with them. Eventually Eleanor would self-actualize at Allenswood, reporting in her memoir “… so I felt that I was starting a new life, free from all my former sins. This was the first time in my life my fears left me.” (Roosevelt, 24) She was even solidifying her relationship with the headmistress, who had invited her to sit beside her at the dining table, as well as offer to take Eleanor traveling! (she described the travel with Madame Souvestre as a “revelation”)
After two years at Allenswood, it was arranged that Eleanor would leave the school and head home to the United States with her Aunt Pussie (maternal aunt). Little did she know, even in her struggle to feel comfortable in her own skin, that love was blooming right around the corner (and not too far from home…)

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