- Long-time companion of Alice B. Toklas, who she met in 1907. They stayed together until Gertrude's death in 1946.
- Attended Radcliffe College (then the woman's annex of Harvard University) from 1893 to 1897, and then two years at Johns Hopkins Medical School, where she failed two courses and left without a degree, citing boredom.
- When she was three years old her parents moved the family to Vienna, Austria, then to Paris, France. They moved back to California when she was four years old (1878), settling in Oakland, where she attended school until 1891, when she was 17 and her father died.
- She sarcastically advocated awarding the Nobel Peace Prize to Adolf Hitler " . . . because he is removing all the elements of contest and of struggle from Germany. By driving out the Jews and the democratic and Left element, he is driving out everything that conduces to activity. That means peace . . . " (New York Times Magazine, May 6, 1934).
- Godmother of Jack Hemingway.
- Was a longtime friend of Ernest Hemingway, who wrote about her salon (a regular gathering of people, generally intellectuals or cultural icons, held for their mutual amusement to discuss culture, current affairs, increase the knowledge and refine the tastes of the participants, and often to bask in their own glow) in his memoir of his life in France, "A Moveable Feast".
- Her older brother Leo Stein moved to London in 1902, and she followed a few months later. They moved together to Paris in 1903, where they settled on the Left Bank, and shared a house and collected art together until 1914.
- Coined the popular phrases "A rose is a rose is a rose is a rose" and "There is no there there" (said in reply to a friend talking about Oakland, CA, who said, "I'm going there").
- Was of German-Jewish ancestry.
- Was an early patron of experimental painting.
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