Remy arrives on Guernsey looking as gaunt and unhealthy as her hospice nurse had warned in her letter. Remy is quiet, but slowly opens up to Kit and Dawsey. Dawsey still remains distant from Juliet, perhaps preoccupied with the comfort and health of Remy. Meanwhile, Isola is pleased to receive a book on phrenology from Sidney in the mail. She proceeds to analyze all of the islanders' head bumps and how the various shapes have affected their personalities.
Mid-month, Juliet writes Sidney of an unexpected discovery that could make Stephens & Stark the most famous publishing house in all of England. Juliet believes that Isola may possess a series of letters written by the famous writer, Oscar Wilde. Juliet comes to such a grand conclusion one night when Isola brings the pack of letters to read aloud at a meeting of the literary society. The letters had been written to Isola's grandmother, Granny Pheen, from a stranger when she was a little girl. Granny Pheen had kept them in a biscuit tin for decades and often read them to Isola as a bedtime story.
Isola tells the society how the letters came about: At the age of nine, Granny Pheen had been crying on the side of the road one day because her cruel father had brutally drowned her beloved cat. A kind and mysterious stranger stopped his carriage to comfort the weeping girl. To Granny Pheen's delight, the stranger told her that the cat actually had nine lives, six of which still waited. He pretended that the cat was being reborn as a wildly adventurous feline named Solange. The stranger then took down Granny Pheen's address and proceeded to write her letters over several years concerning the adventures and perils of Solange. The stories about Solange were full of drama and suspense, and would be read aloud in Isola's family for years to come.
After Isola regales the society with this tale, Juliet notices that the author signed his letters with a grand flourish: O. F. O'F. W. W. Juliet instantly identifies the initials as possibly belonging to "Oscar Fingal O'Flahertie Wills Wilde" and quickly writes to Sidney to find out if Oscar Wilde ever set foot on Guernsey. Sidney's secretary, Billee Bee, discovers that Oscar Wilde potentially visited Guernsey in 1893. If he was the true author, school teachers, librarians, and museums would offer large sums of money for the valuable letters. To the excitement of the islanders, a noted graphologist confirms that the letters were written by Oscar Wilde.
Days later, Juliet receives a strange telegram from Billee Bee that Sidney has been called suddenly to Rome — Billee herself would come to Guernsey to observe the letters. However, an urgent telegraph soon arrives from Susan Scott at Stephens & Stark that Billee is not to be trusted as she is working with muckrake journalist Gilly Gilbert to steal the letters and gain fame. As soon as Juliet receives Susan's urgent telegram, she races to find that Billee has indeed escaped with the Oscar Wilde letters. She recruits the help of Dawsey and frantically searches the island, eventually finding Isola and Kit with the safely recovered letters. The two had hatched an elaborate plan to smuggle Billee into a smokehouse and steal back the letters themselves. Within days, the letters are safely back in Isola's biscuit tin and life returns to normal on the island.
Remy's arrival on Guernsey sheds light on the terrible and lasting effects of life in the concentration camps — particularly, the adverse effects on human emotion. As Remy had witnessed true suffering prior to her arrival, she is inherently cautious to grow close to the islanders. Her unapproachable demeanor is initially a bit unnerving to Juliet, who observes that Remy is stoic and removed from daily life — not unfriendly, but certainly guarded in comparison to other characters who have also experienced the horrors of war.
A pivotal moment for Juliet and Remy occurs while the two sit on the beach watching Kit splash in the waves one afternoon. Remy finally broaches the subject of her friend Elizabeth, sadly commenting that Elizabeth must have danced as freely as Kit at one point. If Elizabeth had only been less headstrong and not attacked the overseer, she could have come home to Kit. Remy essentially asserts that if Elizabeth had just had less heart, perhaps she could have saved her own life in the end. Juliet, on the other hand, believes that the life all around would have been far worse if not for Elizabeth's "heart": her passion, bravery, and steadfast beliefs. Although it brought about her downfall, Elizabeth's heart ultimately unified the islanders in spirit and strength. Perhaps Remy and Juliet's differing opinions about the effects of Elizabeth's "heart" can be attributed to the fact that Remy had actually experienced the cruel realities of a concentration camp — she has been molded by the camp's harsh conditions to give physical survival precedence over emotional clout.
Meanwhile, Juliet's maternal instincts towards Kit develop at a rapid-fire pace. Thanks to her growing attachment to the child, she is emotionally affected by Eben's story of his grandson Eli being sent away at the beginning of the war. Elizabeth McKenna had given Eben's badge to Eli before he was sent away with the other children, explaining that it was a magical badge and that nothing bad could happen to him while he wore it. Eben and Elizabeth could do no more than watch Eli leave. The story holds so much emotional value for Juliet because she cannot imagine the pain of sending a child away. Juliet admits that when she's not with Kit even for a short amount of time, she instinctually worries about her with a mother's intuition. Eben's story functions as more than just another aspect of Juliet's article; it represents Juliet's worst nightmare and proof that she is truly ready to be a parent.
In an even larger sense than Eben's story, Juliet has become preoccupied with Kit's future ever since learning of Elizabeth McKenna's death. Even though the islanders had successfully raised Kit with dedication and love, Juliet cannot imagine Kit's future well being if she were to ever part with the child and return to London. Perhaps more importantly, Juliet cannot imagine her own emotional well being if she were to leave Kit behind. The two provide each other with the unconditional love that had been missing in their lives only months before. Kit also strives to be just like Juliet, growing more and more spontaneous with each passing day — her clever contribution to catching Billee Bee with the Oscar Wilde letters exemplifies this.
Even though Juliet comes to the ultimate conclusion that she wants to be with Kit forever, she still finds herself in a period of uncertainty: How would the other islanders react to her taking Kit to London? Could Juliet ever bring herself to take Kit from her beloved island for a restricted city life? And if the two did move back to London, how could the support system of the Guernsey islanders ever be replaced? Juliet's doubts signify that her character is still on a journey toward self-fulfillment and that she is unsure if the risks for happiness are worth it. She appears to be missing a key element that everyone else senses — she should simply leave London behind altogether. Even so, the realization that she can never leave Kit is a huge leap toward her ultimate destiny.