Characters A First Time for Everything K.L. Walther

Connor McCallister: The Boy Next Door Who Stays a Friend

Overview

Connor McCallister is Mads Fisher-Michaels’s oldest and closest friend, the boy next door who has been a constant presence in her life. For much of the novel, Mads believes she might have romantic feelings for Connor, and the two briefly explore the possibility of dating. Ultimately, however, they recognize that their connection is purely platonic—a bond built on trust, shared history, and mutual respect. Connor’s arc is one of self-awareness and emotional honesty, as he learns that love for a best friend does not have to be romantic to be valuable.

Plot Role

Connor serves as Mads’s primary confidant and stabilizer. He appears in key moments of emotional upheaval—after her disastrous dates, during family tensions, and when she questions her own feelings. He also provides comic relief with his laid‑back humor and his running commentary on Mads’s dating misadventures. More importantly, his presence forces Mads to examine what she truly wants in a relationship, contrasting with the more intense, slow‑building romance she later finds with Marco. Connor embodies the “safe” option that Mads briefly mistakes for love, before realizing that friendship can be just as meaningful.

Motivations and Traits Shown Through Actions

Connor’s actions reveal a thoughtful, loyal, and emotionally open young man. He is not afraid to express his feelings—he tells his mother about losing his virginity the same day it happened, and he openly admits to Mads that he has thought about them being together. His thoughtfulness is demonstrated when he gets up early to buy Mads sticky buns from a local bakery, remembering she had missed them (Chapter 15). He is also considerate of others’ boundaries: when Mads cannot kiss him on their attempted date, he does not pressure her but instead thanks her for her honesty (Chapter 23).

Despite his reputation for always having a girlfriend, Connor is not manipulative or shallow. He genuinely cares about Mads’s happiness, encouraging her to date other guys (like Davis and Robbie) without jealousy. When he breaks up with Lauren after discovering her cheating, he does so without bitterness, expressing a desire to be “the light of her life” for the right person (Chapter 21). This idealism underscores his romantic nature, but also his maturity in accepting when a relationship isn’t working.

Chronological Arc

Connor’s arc follows a clear trajectory from platonic friend to potential romantic partner and back to friend.

  • Early chapters (1–12): Connor is firmly in the best‑friend role. He accompanies Mads to junior prom as her date, offering a safe, fun evening. Mads’s internal narration hints at fleeting thoughts about him, but their dynamic remains unchanged.
  • Mid‑novel (13–16): Connor begins dating Lauren Bitterman, a popular and outgoing girl. Mads feels she has missed her chance, and her jealousy manifests in small ways. Despite this, Connor continues to prioritize their friendship, even letting Lauren’s calls go to voicemail during a beach trip.
  • Confession and brief relationship (21–22): After Lauren’s infidelity, Connor and Mads admit they have both considered dating. They agree to a short waiting period before officially starting a relationship. They share their first official date, and Mads tells her teammates he is her boyfriend.
  • The breakup (23): On their first planned kiss, Mads cannot stop laughing. She realizes she feels no romantic “pull.” Connor admits he feels the same—he loves her but will never fall in love with her. They reaffirm their friendship and head to dinner, relieved.
  • Later chapters (24–27): Connor remains a supportive friend. He is present during Mads’s recovery from ankle surgery and celebrates her new relationship with Marco. Their friendship deepens, now free of romantic tension.

Relationships

Mads Fisher‑Michaels

The core relationship of Connor’s story. They have known each other since childhood, living less than a half mile apart. Their bond is built on shared jokes, emotional support, and a complete lack of pretense. Mads notes that Connor makes her “feel seen, heard, and safe” (Chapter 21). The attempted romance fails because, as Connor says, there is never any “distance” between them—they are too comfortable to create romantic tension. Their mutual decision to stay friends is a mature choice that preserves the relationship’s true value.

Lauren Bitterman

Lauren is Connor’s girlfriend for much of the novel. Mads initially resents her, but Connor’s affection for Lauren seems genuine. When Lauren cheats with Robbie Nielson, Connor ends the relationship without dramatic scenes. He admits things had felt “off” for a while, implying the relationship was already fading. Lauren serves as a barrier to Mads’s hoped‑for romance, but also as a catalyst for Connor’s eventual honesty.

Marco Álvarez

Connor and Marco get along well, sharing a friendly rapport. Marco is the one who suggests that Mads might be meant for Connor, though he later becomes Mads’s love interest. Connor does not express jealousy when Mads begins dating Marco; instead, he offers support. Their easygoing interaction highlights Connor’s lack of possessiveness.

Family

Connor’s family is openly communicative. His parents accept his brother Liam’s announcement of a crush on a boy without hesitation, and Connor himself talks freely about his experiences. This environment has made Connor confident in expressing his emotions, which contributes to his ability to have an honest conversation with Mads about their romantic limitations.

Key Decisions and Consequences

  1. Asking Mads to junior prom (Chapter 8): Connor texts Mads an invitation because he has the most fun with her. This reinforces their close friendship and plants the seed of romantic potential in Mads’s mind, though they remain platonic.
  2. Breaking up with Lauren (Chapter 21): After learning of her cheating, Connor ends the relationship. This opens the door for him and Mads to confess their feelings. The consequence is a brief, awkward romantic period that ultimately strengthens their friendship.
  3. Agreeing to wait before dating Mads (Chapter 21): He wants to separate the new relationship from his breakup with Lauren. This shows his emotional consideration, but also delays the inevitable realization that they lack romantic chemistry.
  4. Honestly admitting he cannot kiss Mads (Chapter 23): In a pivotal moment, Connor thanks Mads for her honesty and admits he feels no romantic “pull.” This decision saves them from forcing a relationship that would not work and solidifies their friendship. The consequence is a deeper mutual understanding and a clearer path for Mads to pursue Marco.

Theme and Symbol Connections

  • Friendship versus romance: Connor and Mads’s arc directly explores this theme. The novel argues that a strong platonic bond can be more valuable than a forced romantic one. Connor’s line “I’m never going to fall in love with you. No matter how much I wish I could” encapsulates this idea.
  • Coming‑of‑age and self‑discovery: Connor’s journey is about learning what he truly wants in a partner and a friendship. He realizes that wanting to be “the light of someone’s life” is different from the quiet contentment of a best friend.
  • Trust and communication: Every major step in Connor’s relationship with Mads hinges on honest conversation—from the junior prom invitation to the final, frank discussion on the porch. Their ability to speak openly prevents resentment and preserves their bond.
  • Growing up and agency: Connor chooses to end a relationship that isn’t working, waits before entering a new one, and ultimately chooses friendship over a romantic label. These active decisions demonstrate his maturation over the course of the novel.

The sticky buns he brings Mads (Chapter 15) can be seen as a symbol of his thoughtfulness and his knowledge of her, but also of the timing that never quite works for romance—he arrives with the buns just as Lauren’s call interrupts Mads’s confession.

5 Questions and Direct Answers

1. Why does Connor break up with Lauren? Connor breaks up with Lauren after discovering she has been cheating on him with Robbie Nielson. He also admits things had felt “off” for a while, and he was waiting for something that “wasn’t coming” (Chapter 21). The infidelity is the final push, but the relationship was already ending in his heart.

2. How does Connor react when Mads laughs during their first attempted kiss? Connor does not take offense. He steps back, listens as Mads explains she cannot kiss him, and then admits he feels the same—he loves her but feels no romantic pull. He thanks her for her honesty (Chapter 23). His calm, accepting reaction saves their friendship.

3. What thoughtful gesture does Connor make during the beach trip? After the beach trip with Marco’s family, Connor wakes up early to go to a local bakery and buys Mads sticky buns, remembering she said she hadn’t had them in a while (Chapter 15). This gesture cements Mads’s belief that no one knows her better.

4. Does Connor ever feel jealous of Mads’s other dates? Connor does not express genuine jealousy. When Mads tells him about Davis and Jacob Bluestein, he focuses on whether the guys treat her well. He admits he thought she was “wasting her time” with them because none were “good enough for you” (Chapter 23), but this is protective friendship, not envy.

5. What does Connor say about why he and Mads will never fall in love? Connor states that Mads is “the smartest, funniest, and most beautiful girl I’ve dated,” but that “for some reason, I’m never going to fall in love with you. No matter how much I wish I could” (Chapter 23). He identifies that the lack of “distance” between them—geographic and emotional—means the romantic spark never developed. They are best friends, not soulmates.

For further exploration, see our pages on the novel’s themes, the ending explained, or our comprehensive character list.