Bailey Bishop

Quick Facts

• Role: Popular, sincere ally who welcomes Libby Strout back to Martin Van Buren High
• First appearance: When Libby returns to school and Bailey immediately reconnects with her
• Key relationships: Childhood friend to Libby; part of a supportive circle with Jayvee De Castro and Iris Engelbrecht; classmate of Jack; foil to image-obsessed peers
• Vibe: Bright, approachable, socially fluent—and actively kind

Who They Are

The essence of Bailey Bishop is uncomplicated goodness put into action. She embodies the novel’s insistence on Seeing Beyond Appearances: popularity doesn’t have to mean cruelty, and sweetness doesn’t have to be naïve. Bailey’s warmth isn’t performative; it’s the spine of her character. She offers Libby not just friendliness but protection, information, and honest accountability—turning what could have been a shallow “nice popular girl” archetype into a reliable, restorative force.

Physical Presence

Bailey’s presence is described as bright and buoyant—“long, swinging hair,” a voice with a cheerful lilt, and a smile that lands like a “lighthouse.” Libby registers her as “too bright” in the best way: a burst of color and optimism that makes rooms feel safer. Even the sensory details—hair that “tastes like a cross between peaches and bubble gum”—underline her cartoon-sunshine aura without trivializing her depth.

Personality & Traits

Bailey’s personality is defined by a rare pairing: social ease plus moral courage. She understands the high school ecosystem and refuses to weaponize it. Instead, she uses her popularity to set a tone of openness, modeling how influence can be protective rather than predatory.

• Genuinely kind, not performative: Unlike the surface-level niceness of Caroline Lushamp, Bailey intervenes when it counts—immediately defending Libby from Sterling Emery and reestablishing their friendship as an action, not a label.
• Loyal and proactive: She goes to Libby’s house to warn her about the “Fat Girl Rodeo” and the social media fallout, then publicly backs Libby (for example, cheering her Damsels audition), turning private care into visible support.
• Socially fluent without cruelty: She “walks into a room expecting people to like her, and they do”—and she uses that capital to normalize Libby’s presence rather than to gatekeep it.
• Optimistic, with ballast: Bailey’s “lilt” and “lighthouse” smile read as joy, but not denial; she sees the ugliness around Libby and works against it.
• Accountable and self-aware: Her apology for not helping Libby in fifth grade shows she has examined her own bystander behavior and chosen to do better. The maturity is in refusing excuses.

Character Journey

Bailey’s arc is subtle: she doesn’t “change” so much as reveal a spine of accountability beneath her glow. Once a passive bystander in elementary school, she confronts that lapse, apologizes without hedging, and becomes an active ally who takes risks for Libby. Each choice—confronting a bully, delivering hard information face-to-face, cheering loudly in public—moves her from the margins of “friendly” to the center of “friend.” The emotional payoff is twofold: Libby receives real support, and Bailey proves that popularity can be ethical leadership.

Symbolism & Themes

Bailey symbolizes the possibility of decency in a harsh social ecosystem. As a foil to Caroline’s conditional popularity, she demonstrates that charisma and kindness can coexist. Within the book’s larger argument about perception, Bailey is a corrective lens: she sees Libby completely and helps others do the same.

Key Relationships

• Libby Strout: Bailey bridges past and present, greeting Libby with immediate warmth and then doing the harder thing—owning her earlier inaction. Their honest conversation repairs a childhood rupture and grounds a friendship built on transparency, not nostalgia. Bailey’s public support helps recalibrate how others perceive Libby.
• Jayvee De Castro and Iris Engelbrecht: With Bailey setting the tone, this group becomes a soft landing spot for Libby. Bailey’s inclusivity turns a cluster of acquaintances into a micro-community where enthusiasm (cheering auditions, showing up) functions as protection.
• Jack Masselin: Bailey’s shock at Jack’s cafeteria cruelty frames his act as a deviation from prankster reputation to genuine harm. Through her eyes, the social stakes of Jack’s behavior sharpen, and the possibility of his complexity is introduced without excusing him.

Defining Moments

Bailey’s defining actions are small but decisive, each one choosing courage over comfort.

• Reconnecting and defending: She tells Sterling Emery to back off and reclaims Libby as a friend on the spot. Why it matters: It signals that Bailey will spend her social capital on protection, not posturing.
• The home visit warning: She goes to Libby’s house to expose the “Fat Girl Rodeo” and the online fallout. Why it matters: She refuses bystander neutrality and delivers information in person, prioritizing Libby’s safety over her own social ease.
• The apology: When Libby asks why she didn’t help in fifth grade, Bailey admits she rationalized her silence. Why it matters: It transforms regret into ethical clarity and cements a trust based on truth.
• Public encouragement: Cheering the Damsels audition and celebrating Libby’s wins. Why it matters: Bailey’s support is visible, not secret—she normalizes respect for Libby in spaces that once excluded her.

Essential Quotes

“Leave her alone, Sterling.” This brief command is Bailey’s ethos in four words—no grandstanding, just intervention. It shows how she wields influence: quietly, promptly, and on behalf of someone more vulnerable.

“I’m just so glad you’re back.” And then she throws her arms around me, and I accidentally suck in some of her hair, which tastes like a cross between peaches and bubble gum. The hug is childlike and unguarded, and the sensory comedy of the hair detail captures Bailey’s bright, almost effervescent presence. The moment turns “popular girl” into “safe person,” collapsing distance with tactile warmth.

“I’m sorry I never came to see you. I should have come to see you. When you were in here. Well, not in here, but in your old house... But we were friends. I should have come.” Bailey refuses to minimize her absence or outsource blame to circumstance. The repetition of “should have” underscores a moral standard she now claims—and intends to live by.

“I don’t know, Libbs. I think I told myself we were friends, but not best friends, and that you seemed like you were okay. You’re still like that... And I felt awful because I didn’t, and then one day you were gone. You didn’t come back.” Here, Bailey names the psychology of bystanding: downgrading closeness, assuming “okay,” and then being paralyzed by guilt. The candor converts private shame into a shared truth, clearing space for a real friendship to begin.