She took took courses in psychology and philosophy growing a strong relationship to her philosophy teacher William James a strong relation to her. James once told her "I hope you will pardon me if I recognize some of the features of my ideal student as your own,"" (Ellensplace). During her finals she left a note to Mr. James saying, " Dear Mr. James, I am very sorry, but I have been to the opera 5 nights this week, and it is such a beautiful day that I could not possibly answer these questions."".
Later she received his reply, "Dear Miss Stein, I entirely agree with you and I think you are a very sensible person. Of course you obtained the highest possible marks on your philosophy paper."" (Muir, ).
After college and a few years traveling in Europe and Africa, Leo and Stein settled at 27 Rue de Fleurus, in Paris. This "27 Rue de Fleurus would be the first real and permanent home for Leo and Gertrude since Oakland in 1891, and one that Gertrude would remain in for almost 40 years.""(Ellensplace) Leo was an art collector, and took pride in discovering new artists, his love eventually spreading to Gertrude Stein. Their house overflowed with paintings by Picasso, Matisse, Renoir, Cezanne, Gauguin and many others. These artists visited the Stein house hold, as well as well known figures of the literary world. A list of visitors to their home would read like a who's who of the literary and art world. Stein had a habit of "adopting- young authors, most notably were Fitzgerald, Hemmingway, and Sherwood Anderson, all who were undoubtedly influenced by her experimental style of writing. .
The closest of these to her were Picasso and Hemmingway. Picasso once asked Stein to pose for him. It took 8 days for him to paint the portrait, and when completed he was told, "But, it doesn't look like her,"" and he replied, "It will."" (Ellensplace). This paining would later be regarded as one of his best works.
