When Phoebe first meets Sam (who becomes her love interest), she observes his “dark, shaggy hair” and “tee-shirt that had a huge rip in the collar” (3). Based on his scruffy appearance and the fact that he appears seemingly out of nowhere in the middle of the night, she becomes suspicious of him, even imagining that he could be a serial killer. His character becomes a study in the often-deceptive nature of first appearances: Sam is a genuinely good guy. He teaches music at an elementary school, not only because he loves music but also because he loves sharing it with children. He’s kind and compassionate and cares deeply about his students and their lives. He hopes to share his passion with them, influencing them to cultivate the kind of life-long interest in music that he has found so enriching.

Sam brings this empathy and kindness to his other relationships too. He hosts a retirement party for a colleague despite characterizing himself as “not great at parties” and gives a heartfelt speech even though public speaking makes him nervous (103). He goes to great lengths to help Conner with his flash-mob proposal, even though the two aren’t close friends. His most recent romantic relationship wasn’t happy, and Sam always felt as though he failed to live up to his ex-girlfriend’s expectations, but he tried his best to make it work, and even though she broke things off, he has few critical words to say about her. He accepts Phoebe’s differences and doesn’t push her into a relationship before she’s ready. He shows emotional intelligence during the many scenes where he shares with Phoebe his assessment of her emotional difficulties and is often more reflective than Phoebe herself.

However, Sam has boundaries and is willing to stand up for his beliefs and advocate for himself. He’s willing to take things slow with Phoebe, but when it becomes evident that the two might not be emotionally compatible, he breaks things off, despite the emotional pain it causes, because he would rather be alone than be in a relationship in which he can’t be his authentic self. He nevertheless remains hopeful that Phoebe will change and reveals to her that he planned to give her some time and space and then see if she might be ready for a more serious relationship. Sam is the archetypal “good guy” whose kindness and empathy make him the one potential romantic partner whom Phoebe can’t shut out forever.

Phoebe’s 23-year-old younger brother, Conner, isn’t close to her initially because after their parents’ divorce, she left to live with her mother and Conner remained with their father. As the novel begins, Phoebe admits to herself that she doesn’t really know Conner, but the two increasingly spend time together, and a much fuller picture of Conner emerges. He too was affected by their parents’ difficult marriage and acrimonious divorce, but he fared better than Phoebe. He sought out counseling and made a concerted effort to process how his parents’ relationship shaped his own ability to relate to people. Conner is self-reflective, thoughtful, and action-oriented, and he successfully re-directed some of his more problematic behaviors. Consequently, he formed a healthy relationship with Shani when the two were still in high school, and they remained together for years before marrying at the end of the novel. Conner’s deep, committed love for Shani is a key facet of his characterization. Initially, Phoebe observes, “It really was sickening, how much he loved his girlfriend” (13). However, as Phoebe confronts her own inability to love fully and authentically, she admits to herself that Conner’s relationship is a model of health and happiness.

Conner is a happy, positive influence on Phoebe, who notes “his optimistic exuberance,” especially because it contrasts with her own dour negativity (2). Conner worked hard in college, and though he doesn’t love his first job, he remains upbeat about his performance and prospects for the future. He loves gaming, and he and Phoebe ultimately reestablish their relationship partly through their shared interest in video games. Phoebe is struck by the fact that Conner spends his free time engaged in activities that make him happy, and she wonders if she might devote too much time to dark ideas and heavy topics. In addition, Conner is thoughtful. The elaborate proposal ideas that he concocts for Shani reflect both his and Shani’s love of whimsy. He stays true to the kind of grand gesture that he knows she’ll find appealing, thus demonstrating not only their shared connection but also his desire to center her in his decision-making process.

Conner’s girlfriend and then fiancée, Shani is a nursing student who views her work as a calling and is dedicated to her career. She’s hardworking, putting as much effort as possible into her studies, and she uses her medical knowledge to help Conner when an accident sends him to Urgent Care. Shani is intelligent and interested in the practical side of nursing, but she’s also kind and empathetic. She’s drawn to nursing as a profession partly because she genuinely wants to help people by providing comfort in addition to medical care during times of crisis and need. Shani brings this same level of compassion to her personal relationships. This is evident to everyone around her, and Phoebe describes Shani as “one of those people you described as sweet and meant it” (31).

A loving girlfriend, Shani has remained in a committed relationship with Conner since high school. Their bond is a key part of Phoebe’s realization that not all romantic relationships resemble her parents’ volatile, emotionally abusive marriage. Shani thus plays a key role in Phoebe’s personal growth process, and Phoebe is ultimately grateful to Shani for the example that she and Conner provide. In addition, Shani helps Phoebe navigate her grief and trauma in more tangible ways. As the novel begins, just after Phoebe and Conner’s father dies, Shani encourages Conner to seek out formal therapy, and though Phoebe is reluctant to follow suit, Shani purchases a book on grieving for her. She understands that both Phoebe and Conner had difficult childhoods and wants to help Phoebe process her experiences. Shani is also fun-loving and bubbly. She adores the flash mob that Sam and Conner organize as part of Conner’s proposal, showing her appreciation for spontaneity and whimsy. Her values, personality, and beliefs are rooted in her upbringing: She’s part of a large, close-knit immigrant family whose supportive, loving character becomes the basis for Shani’s kind and caring nature.

Phoebe reconnects with Allison, her best friend from childhood. The two had a falling out as teenagers and remain estranged until shortly after the novel begins. As an adult, Allison is a librarian whose deep knowledge of literature and sociable nature make her popular with coworkers and library patrons alike. Phoebe notes that Allison “had always been one of the most organized people I know,” and Allison brings her keen organizational ability to her job (34). As girls, Allison and Phoebe enjoyed a mutual love for reading even though they were drawn to different kinds of books. Whereas Phoebe was already interested in dark subject matter because of her difficult childhood, Allison had two loving parents and credits that kind of home life for her sunny disposition and desire to read “happy” books. She had a good relationship with her parents, though she explains to Phoebe that every family has ups and downs: She was adopted, and though she didn’t struggle with abandonment issues or resentment, she often felt culturally out of place as a Korean child in a white family. Still, Allison is grounded and circumspect both as a child and as an adult. She has a loving relationship with her wife, and that example helps Phoebe understand that not all marriages resemble her parents’ chaotic, emotionally abusive relationship.

Allison brings her emotional intelligence to her friendship with Phoebe. She knows Phoebe well and helps her understand how her family trauma shaped her childhood and continued to impact her as an adult. She astutely points out Phoebe’s trouble forming and maintaining emotional connections and helps her engage in the self-reflective process that ultimately allows her to pursue a relationship with Sam. In addition, she helps Phoebe select interview clothing and purchase all the supplies that she’ll need to adopt the cat Lenore. She’s willing to help Phoebe do the heavy, emotional lifting of sorting out her affective life but is also dependable when Phoebe needs practical help.