The characters in Kathleen Glasgow’s How to Make Friends with the Dark form a fragile, fierce constellation of teens and adults learning how to live after loss. At the center is a girl thrust into the foster system, who discovers that grief isn’t the end of her story but the beginning of a new kind of family. Through tangled histories, unexpected alliances, and hard-won trust, these characters chart a path from devastation to endurance.
Main Characters
Tiger Tolliver
Tiger Tolliver is the sixteen-year-old narrator whose world implodes with her mother’s sudden death, propelling her into the bewildering churn of foster homes, social workers, and court dates. Raw and impulsive yet deeply thoughtful, she channels her pain through music and books while wrestling with overwhelming Grief and Loss and the guilt that shadows survival. Her closest bonds—her all-consuming love for June, her anchor-like friendship with Cake, a fragile first romance with Kai, and an initially uneasy connection with her half-sister, Shayna—map the fault lines between her “before” and “after” life. After the catastrophe described in the Chapter 1-5 Summary, she makes self-destructive choices, then slowly learns to endure, finding unexpected community in a grief group and a model of Resilience and Survival. By accepting that family can be chosen as much as inherited, Tiger begins to forgive her mother and herself and to imagine a future not defined solely by loss.
June Tolliver
June Tolliver—Tiger’s devoted, secretive mother—dies of a brain aneurysm early in the novel, but her presence saturates every page in memories, rituals, and revelations. Overprotective because of a traumatic childhood, she cloaks the truth about Tiger’s father and about Shayna, believing secrecy will keep her daughter safe. Only in her posthumous video, discovered in the Chapter 56-57 Summary, does June fully reckon with her choices, offering a complicated act of Guilt and Forgiveness. Her resourcefulness—the bookmobile, the “Jellymobile,” the warm world she builds from very little—becomes both a shelter and a limitation that Tiger must move beyond in order to grow.
Shayna Lee Franklin
Shayna Lee Franklin, Tiger’s twenty-year-old half-sister, crashes into Tiger’s life through a social worker’s phone call and unexpectedly becomes her legal guardian. Sardonic and rough-edged, she’s a recovering alcoholic who has fled an abusive relationship, using bravado to mask bruised vulnerability. Initially a source of chaos, Shayna steadies herself—confronting her ex, Ray, committing to sobriety, and choosing Tiger—until the sisters evolve from strangers into family, as first explored in the Chapter 41-45 Summary. As Dusty Franklin’s abandoned daughter, she reframes what inheritance means, embodying Family and Found Family and proving that caretaking can be a pathway to healing.
Supporting Characters
Dustin "Dusty" Franklin
Dustin “Dusty” Franklin is the absent father tying Tiger and Shayna together: once a teacher, now an alcoholic inmate whose choices wrecked multiple lives. His abandonment of Shayna and silence about Tiger fracture both daughters’ childhoods, turning him into a painful mystery and then a fresh disappointment when the truth surfaces. A tentative phone call in the Chapter 51-55 Summary suggests the possibility of connection, but it is a fragile, imperfect hope.
Cake Rishworth
Cake Rishworth is Tiger’s fearless best friend—blunt, funny, and musically gifted—who keeps showing up with food, a ride, and reality checks. As Tiger’s tether to her “before” life, she models steadfast Friendship even when grief makes Tiger pull away. Their bond bends under strain but never breaks, reminding Tiger that love can be ordinary and reliable.
Kai Henderson
Kai Henderson is Tiger’s childhood friend and first kiss, a sweet, shy boy who represents the teenage life she’s abruptly denied. His panicked choice to leave Tiger at the hospital the night June dies feels like betrayal, deepening her sense of abandonment. Kai’s faltering response to tragedy underscores how unevenly people meet another’s grief.
Lupe Hidalgo
Lupe Hidalgo begins as a beautiful, intimidating bully and reemerges in the grief group with her armor cracked open by the suicide of her brother, Crash. Once enemies, she and Tiger recognize each other as members of the same club no one wants to join, building a wary but powerful camaraderie out of shared pain. Her blunt line—“You’re in the shit now”—names “The Big Suck” and makes room for honesty.
Thaddeus Roach
Thaddeus Roach is the older teen at LaLa’s foster home who takes Tiger under his wing, part cynic and part sage, with scars from severe parental abuse. Introduced in the Chapter 26-30 Summary, he models survival that’s tender, not just tough, and dreams of reuniting with his little sister, Jax. His sibling-like bond with Tiger proves that found family can be steady and kind.
Mae-Lynn Carpenter
Mae-Lynn Carpenter is a quiet, piercingly honest classmate from the grief group whose father died after a long illness. She gives Tiger the first unvarnished map of life after loss—“The Big Suck”—and a friendship where neither has to pretend. Her perceptiveness cuts through platitudes, making space for truth and relief.
Minor Characters
- LaLa: Tiger’s second foster mother, a gentle, hippie-like caregiver who offers a calm refuge and a kinder view of The Foster Care System and Child Welfare.
- Walrus Jackson: The compassionate school counselor who runs the grief group and creates a steady container for teens who feel uncontainable.
- Georgia: Tiger’s first emergency foster placement, whose rigid rules and padlocked fridge embody the fear and scarcity of the system.
- Kendra and Lisa: Teens in Georgia’s home who show Tiger the habits and hard edges that long-term foster care can create.
- Sarah and Leonard: Young kids at LaLa’s house whose stories of neglect amplify the novel’s portrait of systemic trauma.
- Ray: Shayna’s abusive ex-boyfriend, whose reappearance forces the sisters to choose each other and fight for safety.
Character Relationships & Dynamics
Tiger’s closest, most formative bond is with June, whose fierce love and protective secrecy both shelter and limit her daughter. June’s hidden past with Dusty explodes into the present when Shayna appears, redirecting Tiger’s longing for answers into an evolving sisterhood that becomes the story’s emotional future. Dusty’s absence—and then his flawed, belated outreach—threads through all three women’s lives, forcing each to decide what forgiveness can and cannot hold.
Around Tiger grows a circle of chosen kin. Cake stands as the steady, everyday anchor who refuses to let grief isolate her, while Kai marks the tender, unfinished part of Tiger’s adolescence that grief interrupts. In the grief group, Tiger finds peers who speak the same language of loss: Mae-Lynn’s candor offers clarity, and Lupe’s defiance turns into solidarity; together with others like Taran and Alif Parker, they transform a mandatory meeting into a lifeline.
The foster network reveals both harm and haven. Georgia’s house illustrates the system’s coldest edges, whereas LaLa’s home offers warmth, routine, and dignity. Within that sanctuary, Thaddeus becomes a brother figure whose mentorship teaches Tiger how to navigate institutions without losing her heart, and younger kids like Sarah and Leonard remind her that compassion can be a kind of courage.
Conflict catalyzes connection. Ray’s threat forces Shayna to reclaim her safety and commit to being Tiger’s guardian, while Tiger’s own risky spiral—drunk driving and angry outbursts—tests the resilience of every bond around her. Through these fractures, alliances harden into family: sisters choosing each other, friends refusing to leave, and a grieving girl learning she can be broken and still belong.