CHARACTER
The Do-Overby Lynn Painter

Josh Sutton

Josh Sutton

Quick Facts

  • Role: Emilie’s “perfect on paper” boyfriend turned emotional antagonist and eventual friend
  • First appearance: Valentine’s Day, as the centerpiece of Emilie Hornby’s meticulously planned celebration
  • Image: Handsome, academically stylish; the kind of teen who looks already tenured
  • Activities: Debate, DECA, Mock Trial; chats with teachers between classes
  • Key relationships: Emilie; his ex, Macy; the unexpected rival Nick; Emilie’s friends Chris and Roxane

Who He Is

At first glance, Josh Sutton is the curated ideal—smart, charming, ambitious, and tailored to Emilie’s spreadsheet vision of romance. He embodies her belief that love is solvable if you gather the right data and make the right choices, a worldview central to the theme of Fate vs. Control. As the time loop exposes cracks in that fantasy, Josh shifts from dream boyfriend to catalyst, forcing Emilie to admit that a relationship optimized on paper can still be emotionally empty in practice.

Personality & Traits

Josh’s persona blends polish and performance. He’s dazzling in public—quoting authors, winning competitions, executing grand gestures—but less attentive in private. Over the loop’s repetitions, his confidence reads increasingly as self-satisfaction, and his romance as surface-level theater rather than care.

  • Intelligent and ambitious: A star in Debate, DECA, and Mock Trial; he’s the student teachers take seriously, and the one future admissions offices would admire.
  • Curated, “professorial” presentation: He references Shakespeare and Steinbeck in casual conversation, lingers to chat with teachers, and dresses like a young academic—right down to the “good leather accessories.” This cultivated image aligns with Emilie’s ideal of success.
  • Confident to a fault: He carries “the confident swagger of one who was wholly positive that he knew more than everyone else in the room,” which Emilie’s friends, Chris and Roxane, read as arrogance.
  • Superficially romantic: Poems, gifts, and big gestures check Emilie’s boxes—but they often miss her actual needs.
  • Inattentive beneath the polish: His Valentine’s gift—a silver bracelet—ignores Emilie’s severe silver allergy, revealing how his gestures serve the image of romance more than the person he’s dating.
  • Competitive and a bit smug: Emilie notices “a smug look that crossed his face when he was winning,” suggesting he values being right at least as much as being kind.
  • Ultimately self-aware: After the loop, he owns his “complicated” feelings and admits their relationship worked better on paper than in reality—an unexpected, welcome maturity.

Character Journey

Josh begins as “boyfriend perfection,” the gleaming proof that Emilie’s planning works. That illusion dissolves the moment she catches him kissing Macy Goldman, and the time loop forces Emilie to re-encounter Josh until his carefully curated self no longer dazzles. Each repeat shows how their bond is more compatibility résumé than emotional intimacy—polished, impressive, and hollow. When the loop ends, Josh doesn’t contest the rupture; he clarifies it. He admits his unresolved feelings for Macy, acknowledges that he and Emilie were forcing the idea of them, and reframes their connection as friendship. In doing so, he moves from idealized prize to fully human peer—and nudges Emilie toward her Coming of Age and Self-Discovery and, ultimately, toward Authenticity and Identity over control.

Key Relationships

  • Emilie Hornby: Josh and Emilie are aligned in goals and optics—ambition, intellect, polish—more than in vulnerable intimacy. Their eventual breakup isn’t a failure of kindness but a realization that they were collaborating on an image, not building a bond. By the end, their honest conversation makes space for a healthier friendship.

  • Macy Goldman: Macy represents the unresolved past Josh can’t reason away. The kiss in the car isn’t just a mistake; it exposes the emotional truth he’s been managing rather than confronting. His frank admission that things are “complicated” with Macy marks his first real step toward honesty.

  • Nick Stark: Josh’s inadvertent rival. Their limited interactions still highlight a moral contrast: Nick’s protective clarity (“Emilie is too good for you”) underscores how Josh’s carelessness wounded Emilie. Josh’s acceptance of the breakup—and of Nick’s presence—signals his maturation.

Defining Moments

Even Josh’s finest performances can’t withstand the loop’s repetition; what remains are the moments that reveal who he is when the script falls apart.

  • The kiss in the car: Emilie sees him kissing Macy, detonating her “perfect day” and triggering the time loop.

    • Why it matters: It punctures the myth of control and forces Emilie to re-evaluate the relationship’s emotional reality.

  • The intercom breakup: On her “Day of No Consequences,” Emilie publicly calls him a “pompous jag with a stupid car.”

    • Why it matters: Josh becomes the focal point of Emilie’s rebellion against performative perfection; his image cracks under public scrutiny.

  • The silver bracelet gift: He gives Emilie jewelry she’s severely allergic to.

    • Why it matters: A crisp example of his inattentiveness—grand gesture, zero listening—revealing how his romance serves appearances.

  • The final conversation: Post-loop, Josh apologizes, admits his “complicated” feelings for Macy, and articulates that he and Emilie were forcing an idea.

    • Why it matters: This is his most mature moment—he trades performance for candor, enabling both characters to move on without resentment.

Essential Quotes

He X’d every single box on my pre-boyfriend checklist the very first time we met, and he’d been overperforming every day for the entire three months we’d been together. This line captures Josh as a product of Emilie’s method: a relationship chosen by criteria rather than chemistry. His “overperforming” suggests that both of them were sustaining a role—impressive, consistent, and ultimately exhausting.

"She kissed me, Em! I’m sure it looked awful, but I swear on my life. She kissed me." Josh frames the moment as something done to him, revealing his instinct to protect his image first. Whether or not he’s technically truthful, the line exposes his reluctance to own his emotional entanglement with Macy.

"I’ll admit that things are a little, um, complicated with Macy. But I swear to God, I didn’t kiss her." The hedging (“a little, um”) signals discomfort—and truth leaking around the edges. He’s precise about the act while conceding the deeper problem: his feelings aren’t as neat as his reputation.

"I think you’re hot, Em—don’t worry. I just think that maybe we’re meant to be the best of friends." This is Josh at his most honest and considerate. He separates attraction from compatibility, releasing both of them from the performance of perfection and allowing a respectful, realistic redefinition of their relationship.