In Chapter 10, the characters find themselves on a narrow sailboat. The captain cautions them not to lean too far back to avoid tipping over, leading to some light-hearted banter, particularly with Marla, who questions the captain’s joking. Meanwhile, Lila remains composed, chatting comfortably and seeking drinks called “Vacations in a Cup.” This prompts a humorous debate regarding the proper way to pluralize the drinks, demonstrating the tensions and friendships within the group. Marla, having a legal background, argues over the correct terminology, while the others share laughter over shared memories about their college days, drinking stolen church wine.

As they reminisce, an awkward silence grows, revealing Marla’s inability to read the room. Gary, Lila’s fiancé, attempts to soothe the tension, reflecting the dynamics between Lila and Gary. Their relationship seems harmonious, yet beneath it lies Gary’s complicated feelings stemming from past personal struggles. The group’s humor continues, particularly with playful remarks involving past experiences and Marla’s relentless need for validation in her profession.

Phoebe, an English professor, finds herself at the center of the conversation when prompted to clarify the grammatical debate. Her insights bring some clarity and comedic relief, winning her a moment of attention among the group. This lightens the mood, leading to drinking and laughter. However, a darker cloud looms as Marla faces her own issues regarding an expired car registration which distracts from the fun on the boat.

As the story unfolds, Phoebe grapples with her feelings of disconnection and recent trauma from losing her dog, Harry. Her journey in trying to reconnect with her identity and past joys contrasts sharply with Marla’s struggles to maintain her own sense of order and legality. The chapter culminates in an emotionally charged moment where Juice, Gary’s daughter, holds a virtual dog named Human Princess for a makeshift funeral at sea, prompting Phoebe to confront her own loss. There’s a blend of levity and poignancy as characters navigate their relationships, showcasing both humor and the complexities of personal grief amidst a celebratory occasion. Ultimately, the chapter illustrates a delicate interplay of joy and sorrow, friendship and rivalry, laughter, and the underlying weight of loss.