At work, Charlie notices Bailey wanting to intervene as Nekesa and Theo get more flirtatious, but he stops her from interfering and affecting their bet. Charlie has recently bonded with Bailey over reading, and though he hasn’t admitted it, he has seen her social media, particularly her bookish accounts, on which she posts pictures, videos, and reviews of books. When a woman approaches the front desk with a complaint and is rude to Bailey, Charlie steps in to handle the situation.

Bailey returns home from work to find her mother and Scott waiting excitedly in the kitchen. Emily says that Scott has planned a weekend retreat to Breckenridge, Colorado, for fall break.

Bailey is dizzy with shock and dread at the thought of vacationing with Scott. All her fears about Scott uprooting her new life, which she’d just gotten comfortable with, come back in full force. She even wonders if Scott’s involvement with Emily will cause her own father to further withdraw from her.

Bailey says that she’ll have to work, disappointing Emily and Scott. When Emily insists that she get someone to cover her shifts, Bailey bursts out that she doesn’t want to go. She goes to her room, and Emily comes to talk with her. She suggests that Bailey bring Nekesa on the trip to help her feel more comfortable, and Bailey accepts this compromise. After calling Nekesa, whose parents agree to let her go to Colorado, Bailey is more cordial with Scott, thanking him for arranging the trip.

The night before the Colorado trip, Nekesa calls Bailey crying. She reveals that she missed curfew and that her parents aren’t allowing her to go anymore. She suggests that Bailey take Charlie instead. When Bailey insists that Emily and Scott would never allow it, Nekesa suggests that she not tell them—the girls were supposed to drive down separately anyway, so her mother and Scott wouldn’t even know until Bailey and Charlie arrive. Nekesa further suggests annoying Scott by pretending to date Charlie during the trip. This idea sounds ludicrous to Bailey, who shuts it down.

Nekesa invites Bailey, Charlie, and Theo to a group text where they discuss the idea. Charlie agrees to both going to Colorado and fake dating Bailey. When Bailey asks if he needs to ask his mother, Charlie claims that she won’t even notice he’s gone—a post-divorce perk.

Charlie asks if he should shave his beard before the trip, and Bailey says yes because he has “a nice face and the beard hides that” (196). Charlie confesses that he thought she was hot when he saw her at the movie theater last year. In return, she confesses that she thought he was cute too.

Charlie becomes increasingly nervous about the Colorado trip. Theo approaches him during their last shift before Charlie leaves. Charlie likes Theo but also finds him pompous and entitled. Theo reminds Charlie of their bet, and Charlie is confused until he remembers that on their first day of work, Theo mentioned that Bailey was too uptight for any guy to stand a chance with her. Charlie had joked that he could do it, and when Theo bet him $100 to do so, Charlie accepted just to shut him up.

Charlie tells Theo that the bet was only a joke, but Theo says that Charlie is only saying so because he knows he can’t win. Charlie allows Theo to believe that he’s taking the bet seriously.

At work, Charlie and Bailey make a game of racing each other to the bathrooms and back every time they stop for a break, with the winner getting control of the radio. Charlie usually wins, but when Bailey wins by a large margin, she begins to worry about him. He calls her and admits that he’s lost the keys—he dropped them into a urinal and can’t bring himself to fish them out. Bailey enters the men’s restroom to help retrieve the keys and wash them.

Later, they leave for the Breckenridge vacation. As they approach Breckenridge, Charlie mentions that he hopes their weekend away distracts him from some issues at home. His mother is pregnant, and although his sister is excited, he is rattled by the news.

When he changes the subject to Zack, Bailey admits that they haven’t spoken since their breakup. Charlie coaches her, helping to draft a text that he promises will get Zack thinking about Bailey and prompt him to reach out. Bailey follows Charlie’s instructions, asking Zack if he knows her Netflix password and subtly implying that she’s hanging out with someone who watches Breaking Bad. This results in some playful texts between her and Zack, and Charlie instructs her to leave Zack hanging with just a smiley face.

When they arrive at the condo, Bailey decides to go in first and break the news that Charlie has come instead of Nekesa. Emily is angry and tells Bailey to leave until Scott returns from the market. She will talk with him and reach out to Bailey when they’re good to return.

Charlie and Bailey walk to a nearby coffee shop. When Bailey admits to feeling bad and not wanting to hurt her mother, Charlie insists that she needs to look out for herself and brings up their fake-dating plan. He suggests that they hold hands and potentially more to cause further tension. Their conversation is interrupted when Bailey receives a text from her mother—Scott has agreed to have Charlie there, but they’ll need to lay down ground rules.

Bailey and Charlie offer to make spaghetti for Emily and Scott to apologize for taking them by surprise. While they’re cooking, Bailey asks Charlie why he’s always taking TUMS. He vaguely states that he gets heartburn sometimes, but Bailey can tell that her questions make him uneasy.

At the end of the night, Charlie sets up the pullout couch to sleep on, and Bailey goes to her room. He texts her, and they agree to start “dating” the following day at breakfast. When Bailey asks if there is anything she should know about him before they start dating, Charlie admits that his favorite thing about her is “the way [she] always bite[s] the inside of [her] cheek” when he teases her (236). The admission renders Bailey speechless.

Charlie agonizes after sending that text, wondering if he has revealed too much. Eventually, he receives a text back from Bailey, admitting that her favorite thing about him is “the way [his] voice gets deep and crackly when [he’s] tired” (237). Her admission affects him just as much as his affected her. Charlie worries about what he’s gotten himself into.

Bailey is woken up in the middle of the night when her window shatters and a goose flies into her room. Everyone bursts into her room to inspect the commotion, and Scott shoos the goose out. He seals the window with taped cardboard for the night, and the condo owner agrees to send someone out to repair it the next morning. However, Bailey’s room is too cold to sleep in, so she’s relegated to the pullout couch, and Charlie offers to sleep on the floor. Knowing that he has a mild fear of germs, Bailey makes a bed out of the discarded couch cushions so that he won’t have to sleep directly on the floor.