Anne of the Island was published in 1915, seven years after the bestselling Anne of Green Gables. In the continuing story of Anne Shirley, Anne attends Redmond College in Kingsport, where she is studying for her BA.
Anne leaves Green Gables, and her work as a teacher in Avonlea, to pursue her original dream (which she gave up in "Anne of Green Gables"), to take further education at Redmond College in Nova Scotia. Gilbert Blythe and Charlie Sloane are there as well, as are Anne's friends from Queens's College, Priscilla Grant and Stella Maynard. During her first week of school, Anne befriends Philippa Gordon, a beautiful girl whose frivolous ways charm her. Philippa (Phil for short) is also from Anne's birthplace, which is Bolingbroke, Nova Scotia.
The girls decide to set up house in a lovely cottage called Patty's Place, near campus, and center their lives around school, parties, and friends. The girls enter their second year at Redmond happily ensconced at Patty's Place, while life continues in Avonlea. Diana Barry is engaged to Fred Wright and Davy and Dora continue to keep Marilla busy. Gilbert, who has always loved Anne, proposes to her but is rejected ultimately because Anne is so wrapped up in her sentimental fantasies that she isn't yet capable of recognizing real love. Gilbert leaves, embarrassed and disappointed, and Anne and Gilbert drift apart.
Anne's childhood friend Ruby Gillis dies of consumption, very soon after finding her true love. Anne later welcomes the courtship of Roy Gardner, a darkly handsome Redmond student who embodies her romantic image of love and showers her with attention and affection. However, Anne eventually comes to the conclusion that they never connected emotionally and that she had only been in love with the idea of him rather than him for his merits as a person. She only realizes this after two years of courtship, at the last minute during his proposal.
Anne is so ashamed of the way she treated Roy that she feels her entire Redmond experience is spoiled. Deeply disgusted with herself, Anne returns to Avonlea, a "full fledged B.A.", to find everyone happily married except for her. Diana give birth to her first child and Jane Andrews, a schoolday friend, marries a Winnipeg millionaire. Anne is starting to get lonely and nostalgic when she gets word that Gilbert may be dying of typhoid fever. Devastated at the prospect of losing him, she finally realizes the depth of her true feelings for him and prays all night for his recovery and a second chance at love. Gilbert's health returns and after several visits to Green Gables, proposes once more on a late summer walk in the garden.
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