Throughout 1908 and 1909, Woolf was frequently told she should marry. She was, she was told, getting old; at twenty-seven, Woolf was dangerously close to becoming a spinster. Few in the Bloomsbury Group were suitable since many were gay. Woolf cast her eye on Lytton Strachey despite the fact that he was openly gay. He was also a dark, depressive and often impossible man. But he was also brilliant, and that was quite attractive to Woolf. Lytton, for his part, had strong feelings for Woolf, who was an exceptionally beautiful, exceptionally intelligent woman. However, his feelings confused him and led to an uncomfortable situation.

On February 17th, 1909, Lytton Strachey proposed marriage to Woolf, and she accepted. The next day, however, he withdrew his proposal and Woolf graciously agreed to it, saying she was not in love with him. However, she was disappointed as she very much wanted to marry and she deeply admired Strachey. That summer, a man named Hilton Young proposed to Woolf but she did not love him and told him, as excuse, that she could marry no one but Strachey.

Back in London, the Bloomsbury Group began to grow and to flourish. The group, sharing philosophies on art, literature and politics, took as their directive a tenet from philosopher G.E. Moore who believed that these things could only be discussed ideally in a setting in which frankness and freedom from stifling social dictates could exist. The group firmly believed in the social function of art, and many in the circle had a chance to put that into practice, including Woolf and Roger Fry, who would join the group in 1910. Bloomsbury was gaining a reputation in London, and it wasn't a favorable one. Other artists saw the group as a snobbish secret society fraught with pretension and arrogance. Woolf, however, thrived in their company.

In February of that year, some of the Bloomsbury crew pulled a prank on the British Navy by dressing up as Ethiopian dignitaries-even blackening their faces–and taking a tour of the British naval ship, and secret man-of-war, the Drednaught. Woolf took part in this, though others thought it ill advised. It was a success and got into the papers, embarrassing the government.

As Woolf came to the end of The Voyage Out, she fell ill. It was a pattern that would be repeated nearly every time she came to the end of a work. Woolf spent some time in a nursing home in Twickenham, a step down from an insane asylum. That August, Vanessa gave birth to Quentin Bell. Woolf recovered and moved back to London, putting her energies into the Adult Suffrage Movement with her sister. In 1910, Clive, Woolf and Vanessa met Roger Fry for the first time. Roger Fry was a brilliant art critic and painter who was particularly supportive of modern French painting, specifically the then little-known post-impressionists like Cézanne, Picasso and Matisse. Largely due to Roger Fry, 1910 was an aesthetic turning point in England. Fry organized the First Post-Impressionist Exhibition that November, showing the artwork of Van Gogh, Matisse and Picasso, among others. The artwork was unorthodox, shocking and offensive to many art lovers in London. It was an extremely controversial show.

The next year, Clive, Vanessa and Roger Fry traveled to Constantinople to look at ancient art. Woolf chose not to join them until she received word that Vanessa was ill. She met them there and once in Constantinople, got to know Fry and found him delightful. Yet by the time the group returned to London, it was Vanessa who was in love with Fry. He had likewise fallen in love with Vanessa and as a result, Clive and Vanessa's marriage shifted into a union of friendship. From that point on, they had an open marriage, with both Clive and Vanessa taking many lovers. Vanessa, in fact, proposed sexual anarchy amongst the Bloomsbury Group, and promoted a libertarian society. From that point on, it was official: Bloomsbury was scandalous. In July, Woolf entertained her third proposal of marriage, this time from Walter Lamb. She turned him down.

The next year, 1911, upon the expiration of the least at Fitzroy Square, Woolf and Adrian decided to move into a larger house and share it with friends. They found a suitable house in Brunswick Square and offered floors to John Maynard Keyes, Duncan Grant and Leonard Woolf, who was fresh from Ceylon after spending the past seven years there as a colonial administrator. The notion that Woolf, an unmarried woman, was sharing a house with four men was appalling to polite society.

Leonard Woolf had returned to London that June to a Bloomsbury that looked different from the one he'd left, but one which welcomed him back with open arms. In Ceylon he'd been a colonial administrator and was on temporary leave before having to return. During this time, Leonard and Woolf spent a good deal of time together getting to know one another. Leonard fell deeply in love with Woolf almost at once, awed by her beauty and her intellect. Unfortunately, Woolf fell victim to one of her bouts with extreme anxiety and nervousness and had to remove herself from London to rest.

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