Love, loss, and second chances collide in Lynn Painter’s The Do-Over, where a single catastrophic Valentine’s Day refuses to end. Trapped in a time loop, a meticulous planner and a wounded cynic are forced to relive the same twenty-four hours until they finally confront who they are—and who they want to be. Around them, friends and family form a web of support, misunderstanding, and hard-won honesty that grounds the story’s swoony romance and heartfelt humor.
Main Characters
Emilie Hornby
Bold, bright, and relentlessly organized, Emilie Hornby starts the book believing happiness can be engineered: checklists, perfect grades, and a perfect boyfriend will lead to a perfect life. When a disastrous Valentine’s Day loops on repeat, her instincts are to “fix” the day—only to discover that real connection resists spreadsheets. As the loop throws her together with her sardonic lab partner Nick, she begins to question her “Love is for planners” creed and the image she performs for her divorced parents and her friends. The turning-point “Day of No Consequences” lets Emilie try on a truer, messier self, clearing space to repair strained family bonds and to admit that the planned future (including Northwestern and scholarship dreams) matters less than living honestly in the present. Her arc embodies Coming of Age and Self-Discovery as well as the tension between Authenticity and Identity and Fate vs. Control.
Nick Stark
Initially the surly boy Emilie keeps literally crashing into, Nick Stark hides a razor-dry wit and fierce loyalty beneath his walls. The loop peels back his defenses to reveal a grieving younger brother still living in the shadow of a loss that makes Valentine’s Day unbearable. Emilie’s persistence and vulnerability invite him to trade cynicism for connection—especially on the DONC, when he lets himself be seen and shares the truth about his brother. Their growing intimacy teaches Nick that honoring the past doesn’t require closing himself off, and that taking an emotional risk can be an act of bravery. His journey is a quiet, powerful study in Grief and Healing.
Supporting Characters
Josh Sutton
The “perfect on paper” boyfriend, Josh Sutton catalyzes Emilie’s worst day with a betrayal that shatters her curated ideal of romance. Charming, accomplished, and image-conscious, he values the idea of the relationship more than its emotional truth. After the loop, he shows surprising maturity—owning his mistakes and acknowledging that what looked perfect was never real—helping Emilie close that chapter with clarity rather than bitterness.
Chris
Quick-witted and fiercely loyal, Chris is one of Emilie’s anchors as the loop wreaks havoc. He punctures her denial with humor and tough love, encourages her to expect more from the people she trusts, and gets his own sweet subplot with a long-standing crush on Alex. His steady presence—and refusal to be dazzled by surface-level perfection—keeps Emilie grounded.
Roxane
Pragmatic and warm, Roxane completes the best-friends trio with no-nonsense advice and limitless empathy. She’s the first to translate Emilie’s spiraling into clear next steps, reminding her that protecting her own heart isn’t selfish. Her calm compassion provides the counterweight to the chaos of the loop.
Dad (Thomas)
Funny, easygoing, and distracted, Thomas blindsides Emilie with plans to move his new family to Texas—proof that she’s become an afterthought in his busy life with Lisa and the twins. Only when Emilie finally says what she needs does he realize the depth of the hurt he’s caused. His shift from oblivious to engaged underscores that love requires attention, not just affection.
Mom (Beth)
High-achieving and high-strung, Beth funnels her own ambitions into Emilie, confusing success with safety. Her critique-heavy love leaves Emilie feeling managed rather than seen. Confronted with her daughter’s pain, she softens, cooperates with Thomas, and starts choosing empathy over expectations.
Grandma Max
Unapologetically fierce, Grandma Max is Emilie’s safe harbor—the one adult who meets her with unconditional love and a muscle car’s worth of swagger. She’s the first person Emilie trusts with the loop, responding with wisdom, gallows humor, and a battle cry to channel her rage into change. Max’s presence reframes “family” as the people who show up and make space for your truth.
Minor Characters
- Macy Goldman: Josh’s ex whose kiss with him detonates Emilie’s Valentine’s Day and exposes the hollowness of a “perfect” couple.
- Lisa: Emilie’s stepmother; overwhelmed by toddlers and logistics, she inadvertently reinforces Emilie’s outsider status in Thomas’s new household.
- Lauren, Lallie, and Nicole: Hazelwood’s mean-girl trio; they personify the performative judgment Emilie learns to ignore—especially on her DONC.
- Dante: A tattoo artist at 402 Ink and one of Nick’s off-campus friends, offering a glimpse of Nick’s life beyond school and the person he is when he relaxes.
- Tyler: The friendly THRIVE COFFEE cart owner whose easy banter with Nick reveals a lighter, more open side of him.
Character Relationships & Dynamics
At the heart of the novel is the slow-burn bond between Emilie and Nick: forced proximity becomes earned intimacy as they strip away their masks. He sees through her rule-following to the fear underneath; she sees past his sarcasm to the grief he’s been white-knuckling alone. The DONC accelerates their trust—play, honesty, and shared vulnerability stitch together a connection that makes the loop feel less like punishment and more like an invitation to choose each other.
Emilie and Josh, by contrast, expose the gap between appearance and substance. Their relationship runs on checklists, status, and the comforting illusion of compatibility; its collapse is the necessary spark for Emilie’s redefinition of love. Their eventual, clear-eyed parting transforms conflict into closure, allowing kindness to replace idealization.
Friendship steadies the chaos: Chris and Roxane function as Emilie’s reality check and emotional ballast. They challenge her to speak up to her parents, celebrate her courage, and keep her laughing when the day resets yet again. As a trio, they model how supportive friendships can be both protective and disruptive—in the best way.
Family dynamics push Emilie toward honesty. Feeling invisible in Thomas’s new household and micromanaged by Beth, she learns that caretaking other people’s comfort only erases her. Naming her needs forces both parents to recalibrate, while Grandma Max’s fierce loyalty reminds her that love listens first. On Nick’s side, the gravitational pull of his brother’s absence shapes his isolation; friends like Dante and Tyler hint at a chosen-family network he’s too hurt to fully claim—until Emilie helps him imagine connection without betrayal.
Around the edges, school hierarchies and public image—embodied by the mean girls—test whether Emilie will keep performing perfection or live authentically. By the final reset, alliances have shifted from convenience to truth: plans give way to presence, grief to grace, and two teens meet in the messy middle where real love actually grows.