Sidney sends word that he will be coming to Guernsey. Upon his arrival, he spends his days playing with Kit, getting to know the islanders, and having deep conversations with the ever curious Isola. Sidney also observes a budding attraction between Juliet and Dawsey.
Sidney returns to London after a successful trip and reads Juliet's initial chapters. Almost instantly, he has an idea to help Juliet with her writer's block and suggests that Juliet make Elizabeth McKenna the core of her book. After all, essentially all of Juliet's interviews and stories revolve around her. Juliet wholeheartedly agrees and looks to the islanders for their blessing. She prepares to reread her letters, interview more islanders, and observe Elizabeth's personal belongings more closely, all of which lead to even more stories about Elizabeth's time on Guernsey and her relationship with Christian Hellman. Meanwhile, Dawsey finally persuades Remy to visit Guernsey.
Unexpectedly one afternoon, Mark Reynolds arrives in a taxi at Juliet's front door. She and Dawsey had been out walking, and, to Juliet's despair, Dawsey leaves her and Mark alone. Mark pushes marriage on her yet again and accuses her of taking on unnecessary responsibility with Kit. His accusations are certainly a last straw. Two days later, Juliet refuses Mark's proposal for good and sends him on the next flight out of Guernsey.
Sidney's letter to his sister Sophie about his first visit to Guernsey provides an outside's perspective concerning the changes with Juliet. He observes that she seems happier, healthier, and full of her old zest for life. She may, in fact, never return to London, having been seduced by the natural beauty of the island and the kindness of her new friends.
Juliet is easily converting to island life because of her blossoming relationships with Kit and the other members of the society, but also because of her developing romantic interest in Dawsey. Sidney finds Dawsey suitable for Juliet, praising his character as capable, trustworthy, and humorous. Most importantly, Dawsey is different from the other "swine" Juliet has been pursued by in the past. Sidney's opinion of Juliet's past lovers does not stem from jealousy or personal interest; rather, it functions as brotherly concern. The reader learns that Sidney is a homosexual and could never be romantically involved with Juliet, which finally eliminates him as a possible love interest for Juliet. Unsurprisingly, Mark Reynolds does not make any great strides in proving his character or good intentions to Juliet, leading Sidney to believe that the romantic tension between Dawsey and Juliet will progress. Juliet's heightened feelings are especially exemplified by her constant jealousy of Dawsey and Remy's friendship.
Sidney's suggestion that Elizabeth McKenna serve as the core of Juliet's new book firmly establishes the centrality of her character to the novel. Although she is dead before Juliet's adventure even begins, Elizabeth's stories and experiences are relevant to almost every islander. The novel essentially exists in two separate timeframes, Elizabeth and Juliet functioning as the protagonists in each. Just as The Guernsey Literary and Potato Peel Pie Society follows Juliet's journey, so Juliet should immortalize Elizabeth's personal saga in her own book.
Sidney also makes the significant observation that Elizabeth must have felt fear at some point in her life. Juliet already has an image of Elizabeth as strong, willful, and fearless; however, Sidney suggests that Juliet dig further to unveil the darker side of Elizabeth's existence on Guernsey. Although Elizabeth left the island with a close circle of friends, she had arrived on Guernsey with no loved ones and had eventually fallen in love with an enemy soldier. Her character is certainly more multifaceted than Juliet has discovered thus far.
With Sidney's suggestion, Juliet delves further into Elizabeth's life and loved ones — particularly Kit's father, Christian Hellman. The information offered by various islanders about him and other German soldiers further highlight an earlier theme: the underlying humanity of the enemy soldiers. Juliet already knew about Christian's kindness towards Dawsey, but now she learns that he had a regular tendency to offer help to the islanders.
Even beyond Christian Hellman, Juliet learns how German soldiers riding on the back of trucks to the mess hall would often "accidentally" kick potatoes or oranges to Guernsey children on the side of the road. A German soldier even appeared one day on an islander's front stoop with medicine for her sick child. Juliet has never really considered that the enemy could be capable of kindness. Like the islanders, the Germans experienced true suffering: extreme food and water shortages, barren and dangerous conditions, and severe distance from loved ones. The war brought hardships on all sides, and it was often more beneficial to view one another as humans rather than enemies. Juliet did not expect to learn that the Germans helped the islanders in simple and unexpected ways.