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Red spends much of the next morning distracted, thinking about why he agreed to help Chloe in completing the other items on her list. He makes his way to Vikram’s house with plans to paint in his attic. Admiring the light outside the attic window, Red reflects on how his art style has changed and what the implications are. He wonders if he is “ruined, or just changed” (123) and hopes to find out. Vik is surprised that Red is painting again, and Red informs him that he has been painting all along, just not showing anyone his work.
Red decides to draw the cityscape outside the window and decides to not make any adjustments to it—he decides that he should not need to “create a more palatable version of reality” (125) and decides to paint for only himself. The painting he produces is, again, nothing like his old work, and he finds that knowing his style has changed feels “a little like lifting a weight” (126).
When Red pulls out his phone to photograph his newest piece, he sees an email from Chloe. In an overly formal tone, Chloe informs Red that their consultation was a failure due to “lack of focus” (126), and from now on they should communicate solely through email. Rather than take this as a sign she does not want to see him anymore, Red responds in a teasing tone, insinuating that Chloe's distraction is because of her growing attraction to Red.
In a series of back-and-forth banter, Red and Chloe become increasingly flirtatious with one another. Red changes the subject from his website to Chloe’s list, asking her if the items on her list are things that she “fantasizes” (132) about. When Chloe responds that the items on her list are to help make her life more eventful, Red suggests sincerely that the items on Chloe’s list should be things she enjoys, rather than “the stuff other people care about” (134). Chloe tries to keep conversation dispassionate and professional, trying to convince Red to create a social media presence for his art, but Red steers conversation towards less formal topics. He asks Chloe about her decision to always wear buttons, going as far as to create a new nickname for her, “Button,” and telling her that the buttons on her sweaters are “more cute than dignified” (135). In her response, Chloe states that if Red intends to call her Button from now on: “I may sew one onto your tongue” (136). She tempers this playful threat with a compliment on Red’s appearance, admitting that he has “lovely hair” (136).
Red brings up the fact that Chloe has spent nearly the entire day emailing a client, and that they should meet in person tomorrow to discuss the list, to ensure that their bargain is even. Chloe invites Red over to her apartment to take another look at the list and to make good on her threat.
Feeling “alarmingly upbeat” (138) after emailing Red the day before, Chloe spends a sleepless night trying to nurse a numb right foot, which is a side-effect of her condition. In the morning, Chloe is determined to begin working, but a headache and aches cause her to fall asleep. A knock on the door wakes her abruptly and she realizes she has fallen asleep. Unable to regulate her body temperature, another side effect of her condition, Red asks Chloe if she is alright and Chloe feels embarrassed at her attraction to Red.
Chloe and Red sit in her living room and she shows him her Get a Life list. He notes that it seems rather short, and she informs him that she made an edited version featuring only the items that he will be helping her with. Looking at the list, Red asks if she is free the next night to complete the item, “a drunken night out” (145). They decide on Saturday night and Chloe suddenly feels nervous realizing how soon that is. Sensing her anxiety, Red reminds her that she does not have to do any item on the list that she does not want to, but Chloe insists that she will.
Red asks her how long she would like to go camping for, and they decide to go overnight Saturday to Sunday the next week. With that decided, Red becomes serious and says that he needs to ask her something. She becomes visibly nervous, and he tries to soothe her anxiety by reminding her that they are friends. This prompts Chloe to remind Red “A week ago you barely even liked me” (150) and Red reminds her that she did not like him either, but now he finds her “funny and secretly sweet” (150). Chloe is happy to hear this, knowing now that the tone of his emails yesterday was not just part of his natural charm.
With their friendship confirmed, Red asks her if she can tell him what the risks are of her condition so that he can be better prepared to help her. Chloe tells him that she has fibromyalgia and understands her limits, and that the list is not really about her disability. She says that she used to be “A socially inept control freak” (152) and Red asks what changed to make her view her life in terms of a before and after. He admits that he has some experience with the feeling himself, and she says she recognizes it in his paintings, admitting that she has researched his artwork and saw the difference in his older work. With this new vulnerability between them, Red asks Chloe to tell him more about her past.
Chloe explains her life before her fibromyalgia diagnosis. She used to have a wide social circle and was even engaged. Things changed for Chloe when she was diagnosed with pneumonia and ended up in the hospital. After she left the hospital, her condition never improved, and she developed more symptoms such as exhaustion and headaches. Chloe explains that apart from her family, almost no one in her life understood or even believed her during this time, and that even doctors told her parents that she should have an evaluation for mental illness.
Red’s heart breaks as he listens to Chloe’s story and the abandonment and disbelief she has endured. He affirms her feelings and is furious to learn that Chloe’s former fiancée, Henry, didn’t believe what she was feeling. Chloe finishes her story by explaining that her list is about getting her bravery back. While she has developed skills and tools to manage her condition, she still feels “like a part of me hasn’t caught up with that. Like I’m still afraid of myself” (158). Red reaffirms that the people in her life who left are unworthy of her and tells her that she should make new friends. Red also notices that Chloe is sweating and appears to be at risk of overheating, so he tells her to take off the fluffy robe she wears.
Chloe insists that she is fine despite evidence to the contrary, and Red presses his hand to her burning cheek. Red notices Chloe is aroused, and he bends his head to rest against her temple. Red then takes her hand in his and kisses her jaw. Chloe finds herself almost overcome with arousal and she moans as he licks her earlobe. Red states that he wants to kiss her and asks if he can. Fearing that she may lose control if she says yes, Chloe asks him to stop, which he does at once. Chloe restrains herself from pulling him back in and kissing him, remembering the “meaningless sex” part of her list, but stops herself knowing that “nothing would be meaningless with someone like Red” (166). After they both take a moment to calm down, Red asks Chloe if she is okay. She insists that she is fine and says she will see him Saturday for their night out. Red asks if she still wants to go and she affirms that yes, she does. When he tries to mention the near kiss, she nearly pushes him out of the apartment insisting that she is “a poor, disabled woman who is not to be harassed with unnecessary conversation” (167). Red laughs and she pushes him out of the door.
Two days later, Chloe reviews the list of bars that Red chose for their night out. She cannot help but notice that each of the bars are close together, so that she will not become tired walking between them. This discovery momentarily pleases her before she reminds herself not to become too emotionally involved with Red, believing that he, like everyone else, will eventually exit her life.
On the phone with Gigi, Chloe watches Smudge clean himself. Gigi asks her why she is upset, which Chloe denies, although she is upset after taking Smudge to the vet and finding out that he is microchipped and does in fact have an owner. Gigi can sense that something is wrong and insists Chloe explain. Chloe tells her that Smudge’s owner’s name is Annie, and that she is currently on vacation. Chloe explains that when Annie returns, she will have to meet up with her to give Smudge back. As Gigi and Chloe expound on Annie’s unfitness to be a mother, a knock on the door cuts their call short. Gigi senses that the interruption is because of a man, which Chloe denies, hangs up, and opens the door for Red.
Red knows Chloe is upset about Smudge before he arrives at her apartment that evening because she emailed him earlier in the day. Knowing that she will be upset, Red promises himself not to say anything to her unless she brings it up. When he sees her holding Smudge as she opens the door, however, he at once asks her if she is okay. She says she does not want to talk about Smudge, and her sharp tone upsets him because he knows it means she must be dealing with her emotions alone. Still wearing a robe, Chloe tells Red she is going to dress and leaves him in the living room.
While Chloe dresses, Red creates a list of all the reasons why he “shouldn’t lust after Chloe anymore, even if he desperately wanted to, really enjoyed it, and wasn’t totally sure he could stop” (175). His reasons range from Vik disapproving of him dating a tenant, to her shutting down his first advance, to thoughts of her becoming too distracting during the day. Chloe interrupts his train of thought by entering the living room, her beauty stopping him. She asks him if her outfit is proper, and to keep calm he says, “It doesn’t have buttons, but it’ll do” (176). She laughs and the two make their way out of the apartment.
Chloe and Red continue to develop both as individuals and in relation to one another. The flirtatious email exchange they share in Chapter 8 leaves little room for question that their relationship has taken a turn for the romantic. This is most clear in Red christening Chloe with her new nickname, “Button” (136) and the evolution of Chloe’s email signatures, which begin as a chilly and distant “Rgs.” (127) to “Yours” (137) over the course of their exchange.
While teasing banter remains foundational to their interactions, in their email conversations, there are moments of sincerity that come through, such as when Red suggests that Chloe put items on her list that she genuinely wants to complete: “[D]on’t you think, if your life ever flashes before your eyes again, you should remember all the shit you enjoyed? Rather than the stuff other people care about?” (134). This quote illustrates Red’s own developing sense of self and determination to live his life on his own terms rather than basing his self-worth on the opinions of others. As he reflects on the noticeable change in his art style since leaving London and his traumatic relationship behind, at first, he thinks to himself, “So he had his answer. He’d lost himself” (125). Instead of letting this fact derail him, however, Red finds that “Oddly, it didn’t choke him. In fact, knowing it once and for all felt a little like lifting a weight” (126). Here, Red chooses to embrace this unfamiliar version of himself, and finds that it feels lighter to cast off the expectations of the past.
Red’s renewed sense of self enables him to create space for Chloe to be vulnerable and expose her own traumatic past. As Chloe explains how she developed fibromyalgia, how her fiancé left her when it became clear, she would never get “better” and he refused to believe and validate her, Red sees how lonely Chloe has been. His anger towards those that left Chloe in the wake of her illness also shows his feelings for Chloe as someone that he cares about and wants to validate.
Red notices Chloe’s well-being, noting “her pain a mile off” (159) and sensing how upset she is when she tells him she must return Smudge to the rightful owner. While Red is caring towards everyone, these chapters reveal a special sense of wanting to care for Chloe. As Chloe and Red’s conversation crosses a threshold of vulnerability, so does their physical relationship. Chloe and Red nearly kiss, and though Chloe’s fears of giving in to the intensity of her attraction to him causes her to stop things from progressing, this section shows a turning point in their relationship that they will not turn back from.
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