The perspective shifts to Colin “Fitz” Fitzgerald, who is at a loud New Year’s Eve party in a Brooklyn bar. He feels out of place and is trying to avoid the crowd when Summer approaches him. She asks him to dance, but he refuses. She playfully calls him a curmudgeon and accuses him of always running away from her. Internally, Fitz acknowledges his conflicting feelings—intense attraction mixed with an instinct to flee what he perceives as her drama, a conflict he calls the “Summer Dilemma.”

During the party, Fitz’s teammate Hunter reveals that he and Summer attended the same prep school. Fitz also reflects on the vast difference between Summer’s family wealth and his middle-class upbringing, feeling unsettled by the fact that Summer lives in penthouses and owns clothes that cost thousands of dollars. As Fitz attempts to ignore his attraction to her, Summer teasingly suggests they should make out.

Summer’s suggestion that they make out, flusters Fitz, but she clarifies it was mostly a joke meant to make him blush. Several of Dean and Fitz’s friends and former teammates, including Garrett Graham and his girlfriend Hannah Wells, arrive and interrupt them. Hunter flirts with Summer who asks him who he plans to kiss at midnight. He declares he avoids New Year’s kisses because he thinks women read too much into them.

Later, while Summer is in the restroom, Garrett asks Fitz if he’s interested in Summer. Fitz dismisses Summer as a “party girl,” describing her as “fluff” and “surface level,” definitely not his type. Garrett sees through this, accusing Fitz of simply trying to convince himself not to like her and correctly guessing that Fitz has a crush. Persuaded by Garrett’s argument, Fitz decides to stop fighting his feelings and resolves to kiss Summer at midnight. However, as the countdown ends, he spots her across the crowded room, sharing a kiss with Hunter.

On New Year’s Day morning, Fitz wakes up alone in his hotel room, having left the party before 1 am. He scrolls through numerous messages and missed calls from friends and family but notes the absence of any communication from Hunter. As he checks his texts, he reads a message from Dean. Dean asks for a huge favor, inquiring if Fitz and his roommates are still looking for a fourth person to fill the empty room in their house.

Two weeks later, Summer has an unpleasant meeting with Briar’s Assistant Dean, Hal Richmond. He warns her about academic probation, and his criticism of her ADHD and difficulties with written assignments leaves her feeling deeply embarrassed. Citing her family’s financial donations and his skepticism about her admission, Richmond informs Summer that he will be her personal academic advisor to closely monitor her progress and conduct.

After the meeting, Summer is plagued by the memory of Fitz’s hurtful comments from New Year’s Eve, where she overheard his conversation with Garrett. Dreading the prospect of living with him, she hesitates in the campus parking lot, indecisively locking and unlocking her car to delay going home. Her strange behavior attracts the attention of another student, Brenna Jensen, who approaches her. To further postpone the inevitable confrontation, Summer offers Brenna a ride into town.

In the car, Summer tells Brenna that she’s avoiding her new roommates. She recounts the events of New Year’s Eve: having a crush on one of the guys, overhearing his insulting comments about her, and then impulsively kissing his roommate at midnight. When Summer identifies her crush as Fitz, Brenna recognizes the name. She reveals that her father is Chad Jensen, the head coach of the Briar men’s hockey team, and that she knows Fitz, Hunter, and Hollis.

During the conversation, Summer accidentally mentions the guys’ ski trip—a violation of team rules—not yet knowing Brenna is the coach’s daughter. Brenna promises not to tell her father. Before getting out of the car, Brenna urges Summer to go home and face the awkward situation head-on. She invites her to the Briar vs. Harvard hockey game the following night. Resolved, Summer drives to her new house.

Fitz, Hunter, and Hollis return to their townhouse after a secret ski trip in Vermont, which is against team rules. They agree on a cover story: They spent the weekend in New Hampshire playing Monopoly. Still in the Land Rover, Hollis raises the idea of dibs on Summer; Hunter tells him hands off, noting the New Year’s kiss cemented his claim, though he first clarifies she is not a piece of meat. Summer greets them, and her initial exchange with Fitz is brief and awkward.

Once in his room, Fitz takes a call from his friend Morris, who is beta-testing Legion 48, a role-playing video game that Fitz designed. Morris gives the game rave reviews, which lifts Fitz’s spirits. However, his good mood quickly dissolves when he hears the low murmur of Hunter’s voice followed by Summer’s laughter. Their easy camaraderie makes him tense and unhappy.

Hunter goes to Summer’s room to discuss their New Year’s kiss. They both agree it was not a big deal, but the sexual tension between them is palpable. Later that night, unable to sleep, Summer goes to the kitchen for a snack wearing only a thin, see-through T-shirt. She finds a shirtless Fitz at the table drawing in a sketchbook and is immediately struck by her intense physical attraction to him.

Fitz asks her to keep their forbidden ski trip a secret, but Summer confesses she already told Brenna, the coach’s daughter. Fitz curses and expresses concern that Brenna is “dangerous when she loses her temper.” (65). Summer notices he’s reading a fantasy novel from a series she loves. When she mentions she has also read the books, Fitz’s skeptical reaction implies he believes the material is too “dense” for her to comprehend. Furious at being judged yet again, Summer angrily tells him, “I know how to fucking read” (67), before storming out of the kitchen.