Chapter 18 begins with Lila visiting Phoebe in the morning, on her way to the flower vendor, where she casually mentions a power outage that has affected the flowers. Lila, without discussing the complexities of blending their families, asks Phoebe to accompany Gary for errands due to his back injury from surfing. With a humorous reference to herself in the third person, Lila brushes off concerns about Gary’s condition and states her intent to keep him occupied. Despite her calm demeanor, Phoebe dreads spending the day with Gary, as she has been trying to move on from him. This reluctance to spend time with Gary is coupled with an underlying tension, as Phoebe must navigate her feelings while attempting to honor her role in the situation.

As they set off on their errands, Phoebe is conflicted, feeling both anxious and excited about a public speaking engagement later that day. Throughout their time together, she and Gary engage in banter, discussing their mutual discomfort with aging and the physical pains that come with it. They laugh about their shared experiences of bodily changes, turning what could have been complaints into a humorous exchange. This lighthearted conversation helps ease some of the tension between them, providing a sense of camaraderie before the weight of the day’s responsibilities settles in. Despite the playful moments, Phoebe remains aware of the underlying emotions she is trying to suppress, particularly the complexity of her feelings for Gary.

After picking up preordered liquor from a store, Phoebe receives an unexpected text from Geoffrey, the mansion keeper, regarding a caretaker position at Newcombe Mansion. Intrigued by the opportunity, Phoebe decides to meet Geoffrey after she drops Gary off. Upon arriving at the mansion, she is greeted by Geoffrey, a charming southern gentleman who explains the requirements for the caretaker position. Phoebe is eager to discuss her research on historical buildings, something that sparks a renewed passion in her during the interview. Her enthusiasm for the subject gives her a sense of purpose, offering a brief escape from the emotional complexity of her day. As the conversation shifts to the mansion’s potential and her qualifications, Phoebe begins to envision a new path forward, one that could provide her with a fresh start away from the current emotional turmoil.

While exploring the mansion, Phoebe and Gary discuss the lavish interiors, leading them to philosophical conversations about happiness and art collection. Gary, in a moment of unexpected vulnerability, admits that he feels happiness in the present moment, offering a rare glimpse into his emotional state. This honesty deepens their connection, as Phoebe begins to realize the weight of her unresolved feelings for him. Despite their comfortable exchange, the reality of Gary’s impending marriage looms large, and Phoebe’s heart aches at the thought of him marrying someone else. These moments highlight the deep emotional pull she feels toward Gary, complicating her ability to move on, especially as they share such intimate and meaningful conversations.

They continue their day by stopping at Gary’s tailor, where Phoebe’s mixed emotions resurface. She begins questioning whether she can truly move forward from her current life as a teacher to embrace a new life in Rhode Island. The thought of leaving her career behind conflicts with the powerful pull she still feels toward Gary, creating an emotional tug-of-war. Their shared moments throughout the day blur the lines between friendship and something deeper, making Phoebe question whether her feelings for Gary are just remnants of the past or if they still hold significance in her life. This internal conflict continues to build as the day goes on, making her feel more uncertain about her path forward.

At the barber, Gary opens up further, sharing a moment of vulnerability about how much he misses teaching. In this conversation, they connect over the pretense they both have had to maintain in their professional lives, revealing the pressures they each face. This mutual understanding brings them even closer, but the reminder of Gary’s impending marriage remains a constant undercurrent, making it difficult for Phoebe to fully embrace their connection. She recognizes the delicate balance between her loyalty to Lila and her undeniable feelings for Gary, knowing that these emotions complicate her role as maid of honor in his upcoming wedding.

As they return to the hotel, the atmosphere between Phoebe and Gary shifts, filled with unspoken feelings and powerful emotions. Lila’s unexpected appearance amplifies Phoebe’s fears, reminding her of the impending wedding and the complicated role she will play in it. The realization that while she and Gary have shared a meaningful day together, the reality of his marriage to Lila is fast approaching, hits Phoebe hard. She must now prepare herself for the role she has agreed to as maid of honor, all while grappling with the unresolved emotions she harbors for Gary. This chapter leaves Phoebe in a state of emotional flux, torn between her loyalty to her friend and the lingering love she feels for the man about to marry someone else.