Woolf encountered the woman upon whom she would model Sally in Mrs. Dalloway only briefly. Madge Symonds was married to one of Woolf's uncles, and she was a beautiful, thoroughly modern woman who was a writer. Woolf found her enchanting and may have fallen in love with her. She was one of a number of captivating women who would capture Woolf's attention and find their way into her fiction.

In 1901, Thoby, who was at Cambridge, met a number of extremely intelligent, interesting young men-fellow students. Lytton Strachey, Leonard Woolf and Clive Bell were among them. Woolf and Vanessa would not meet these young achievers for a few more years, however. The sisters were still studying at home during the days and completing household chores in the evening while their brothers were being educated at the best schools England had to offer. For the rest of her life, Woolf would feel herself behind the curve and poorly educated because she was not granted the opportunity to attend college simply because she was a female. It seemed a bitter injustice, and she never forgot it.

Around this time, two more fascinating women came into the sisters' lives. Kitty Maxse was an intelligent, calm, lovely woman who was married to the editor of the National Review, Leopold Maxse. Julia had introduced them and took pride in having successfully matched them. Although Kitty and Woolf didn't quite hit it off (she found a confidante, however, in Vanessa), Kitty was likely the model for Clarissa Dalloway. Violet Dickinson first visited the family at their new summer place in Fritham in 1902. Dickinson was over six feet tall, was an unusual and intelligent woman and evoked very complex feelings in twenty-year-old Woolf. In the letters the two women shared, it is fairly clear that Woolf was deeply in love with Violet, though that love was likely never consummated. Violet would remain a friend of Woolf's for many years, though they would drift apart when Woolf began her foray into the Bloomsbury Group.

That same year, 1902, Leslie Stephen grew more frail and more ill, and it was clear that he was dying. Though he hung on for about a year, Woolf and Vanessa had to deal with a series of already grieving, wailing female family relatives who taxed the girls' nerves. On February twenty-two, 1903, Leslie Stephen died.

Woolf was emotionally distraught and exhausted by the year she had spent watching her father die. That year, she and her four Stephen siblings moved out of the Kensington house at twenty-two Hyde Park Gate and bought a house in then-shabbier Bloomsbury. Before moving in, the siblings traveled to Italy for a holiday. Woolf, still emotionally delicate, was weary and irritated halfway through the trip, and wanted to go home. While Vanessa felt somewhat freed by her father's death (after Stella died, he'd made Vanessa his crutch and made many demands on her time and emotions), Woolf was desperately sad. The group stopped in Paris and met with Thoby's friend and painter Clive Bell.

Almost as soon as the siblings returned to London, Woolf had a breakdown. She began to hear voices, her pulse raced, and her heart beat at what seemed a dangerous pace. Violet arrived in London to take Woolf to her home at Burnham Wood, and there Woolf first attempted suicide by throwing herself out of a second story window. She was unharmed by the incident and slowly began to recover.

In 1904, Woolf sent an article she'd written about Haworth Parsonage in Yorkshire, the Bronte sisters' family home, to a London weekly called The Guardian. The editor accepted it happily and from that point on, Woolf was a regular contributor. She was happy to have found an outlet for her early works of journalism. She was soon regularly employed to write reviews as well as articles. In the meantime, the Stephen children had comfortably settled in their new home at forty-six Gordon Square in Bloomsbury. Family relatives, including the Duckworth half-siblings, had been shocked by the Stephens' decision to move into Bloomsbury, which was certainly a step down from the posh Kensington neighborhood in which they'd grown up. But Vanessa, Woolf, Thoby and Adrian felt stifled by the stiff Victorian social code that they'd suffered their entire lives. The move into Bloomsbury was a break from social shackles, in many ways. Thoby began to invite his Cambridge buddies to the house, and instituted Thursday evening get togethers. Clive Bell, Sydney Saxon-Turner, Leonard Woolf, Lytton Strachey, Desmond MacCarthy and John Maynard Keyes-a veritable laundry list of the most influential painters, writers and thinkers of the next thirty years-converged on forty-six Gordon Square. Woolf and Vanessa sat in on the gatherings and were slightly awed by Thoby's friends.

The men were initially extremely reserved, often sitting in chairs silently for hours. They were cerebral, and they expected the same of Woolf and Vanessa. It was a welcome change from the social expectation that women simply marry and master social skills. Thoby's friends respected Woolf and Vanessa's great intelligence and talent and expected them to make something of it. While the circle-christened the Bloomsbury Group-grew closer and more intense, those outside of it grew jealous and judgmental. Many of Woolf's non-Bloomsbury friends were not impressed with Thoby's friends. They found them untidy and impolite. Even more shocking was the fact that Woolf and Vanessa were staying up until all hours conversing with them and swapping philosophies and ideas. For young, unmarried women, this was unacceptable social behavior at the time.

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