Plot Summary
Sunrise and Goodbye
Starlet's world is shaped by the early loss of her mother, whose final letter and recipe box become a touchstone for comfort and memory. The story opens with Starlet's longing for her mother's presence at every milestone, especially as she approaches her carefully planned future. The ache of absence is palpable, and the promise to "find me in the sunrises" becomes a motif for hope and healing. This chapter sets the emotional tone, introducing the central theme of grief and the search for connection after loss, as Starlet clings to her mother's memory while trying to move forward.
Shattered Plans, Shaky Hearts
On her 21st birthday, Starlet's meticulously ordered life collapses when she discovers her boyfriend cheating. The humiliation and heartbreak force her to confront the fragility of her plans and the emptiness beneath her perfectionism. Her best friend Whitney tries to lift her spirits, pushing her to attend a frat party and embrace spontaneity. Starlet's identity, so long defined by doing the "right" thing, is suddenly in flux. The pain of betrayal is compounded by the absence of her mother, whose guidance she craves. This chapter marks the first crack in Starlet's self-image and the beginning of her journey toward authenticity.
The Night That Changed Everything
At the party, Starlet meets Milo—a brooding, magnetic stranger with a sharp tongue and haunted eyes. Their banter is electric, laced with innuendo and vulnerability. Both are reeling from recent wounds, and their chemistry is undeniable. In a moment of reckless abandon, Starlet chooses to live outside her comfort zone, leading to a night of intense, transformative intimacy. The encounter is raw, healing, and destabilizing, leaving both shaken. For Starlet, it's a taste of freedom and self-discovery; for Milo, it's a rare moment of connection that stirs something long dormant.
Aftermaths and New Beginnings
The morning after, Starlet is both empowered and unsettled by her actions. She returns to her routine, but the memory of Milo lingers. Meanwhile, Milo, who uses sex and substances to numb his pain, finds himself unable to forget Starlet. Both are haunted by the night, unsure if it was a mistake or a catalyst. Starlet seeks comfort with her father and the tattoo parlor "family," while Milo spirals, his grief for his mother and fractured relationship with his father deepening. Their paths seem destined to cross again, but neither anticipates how soon or how complicated it will be.
The Boy Called Dick
Milo's perspective reveals a young man drowning in grief, anger, and self-destruction. His mother's death has left him adrift, his father lost to alcoholism. Milo's reputation as a "manwhore" is a shield against feeling, but Starlet's impact lingers. His friends try to reach him, but he resists vulnerability. The anniversary of his mother's death looms, intensifying his depression. Milo's world is cold, his coping mechanisms failing, and the memory of Starlet is both a comfort and a torment. This chapter delves into the psychology of loss and the ways we sabotage our own healing.
Collisions and Consequences
Starlet begins her student teaching at a local high school, only to discover that Milo is her student. The shock is mutual and immediate. Both are horrified by the implications, but the connection between them is undeniable. They agree to keep their past a secret, but the tension simmers beneath every interaction. Starlet is torn between her professional responsibilities and her growing feelings; Milo is both antagonistic and vulnerable, pushing her boundaries while craving her care. The stakes are raised, and the line between right and wrong blurs further.
Unlikely Tutor, Unlikely Student
Forced to tutor Milo to save his academic future, Starlet is drawn deeper into his world. Their sessions are fraught with unresolved desire and emotional landmines. As they work together, they begin to share their grief—Starlet's for her mother, Milo's for his. The act of teaching and learning becomes a form of mutual therapy. Starlet's compassion chips away at Milo's defenses, while his honesty challenges her to confront her own pain. Their relationship grows more complex, oscillating between professional, platonic, and something more.
Boundaries and Blurred Lines
The secrecy of their connection intensifies their bond. Late-night texts, shared confessions, and stolen glances blur the boundaries between teacher and student, adult and adolescent, healer and wounded. Both are terrified of the consequences but unable to let go. Starlet's anxiety mounts as she fears for her career and reputation; Milo's need for her deepens as his home life deteriorates. The outside world—friends, family, school—presses in, threatening exposure. The tension is both erotic and existential, as they teeter on the brink of revelation.
Grief's Heavy Winter
The first anniversary of Milo's mother's death brings his pain to a breaking point. He spirals into substance abuse and nearly overdoses at school, with Starlet the only one able to reach him. Their shared experience of mother-loss becomes a lifeline, but also a source of guilt and fear. Starlet risks everything to protect him, even as she questions her own judgment. The chapter is a meditation on the different ways grief manifests and the impossibility of "moving on" without first moving through.
Secrets in the Library
In the aftermath of Milo's crisis, Starlet and Milo grow closer, sharing stories of their mothers and the small rituals that keep memory alive. Their study sessions become a sanctuary, a place where they can be honest about their pain and hopes. Starlet stands up for Milo against a dismissive teacher, and Milo begins to trust her with his vulnerabilities. The risk of discovery remains, but the need for connection outweighs the fear. Their relationship, though still forbidden, becomes a source of genuine healing.
The Year Without Mothers
Both Starlet and Milo reflect on the ways their mothers' deaths have shaped them. Starlet's perfectionism is revealed as a coping mechanism, while Milo's self-destruction is a form of protest against a world that feels indifferent. They find solace in each other's understanding, but also recognize the danger of becoming each other's only support. The chapter explores the intergenerational impact of loss, the longing for parental approval, and the slow, uneven process of rebuilding a sense of self.
Ice Caves and Melting Walls
Starlet and Milo embark on a photography trip to the ice caves, a symbolic journey through the coldest winter of their lives. Away from the pressures of school and society, they allow themselves to be fully present with each other. The natural beauty around them mirrors the beauty they find in vulnerability and trust. Their physical intimacy is rekindled, but now it is layered with emotional depth. The trip is a turning point, marking the beginning of true partnership and the possibility of a future together.
Becoming Secret Friends
Returning from their trip, Starlet and Milo attempt to set boundaries—"secret friends" with rules to protect themselves and each other. But the heart refuses to be managed. Their connection deepens, and the secrecy becomes both a thrill and a burden. Outside pressures mount: Milo's father's decline, Starlet's academic struggles, the ever-present threat of exposure. The chapter explores the tension between desire and duty, and the ways we rationalize our choices when love is at stake.
The Coldest Confessions
Milo is diagnosed with a degenerative eye disease, facing the prospect of eventual blindness. The news devastates both him and Starlet, testing the strength of their bond. Milo's fear of becoming a burden leads him to push Starlet away, while she struggles with her own sense of helplessness. Their roles shift—Starlet becomes the caretaker, Milo the one in need. The chapter is a raw exploration of illness, dependency, and the fear that love may not be enough to save us.
Breaking, Healing, Breaking Again
Milo's father is hospitalized after a drunk driving accident, forcing Milo to confront the possibility of losing another parent. Starlet stands by him, but the strain of constant crisis takes its toll. Both are forced to reckon with their own needs and limitations. The cycle of breaking and healing repeats, each time leaving new scars but also new wisdom. The chapter is a testament to the resilience of the human spirit and the necessity of letting others in.
The Letter and the Recipe Box
Milo discovers his mother's recipe box, each card inscribed with a personal note. Cooking becomes a ritual of remembrance and a way to reconnect with the past. Starlet, too, finds comfort in family traditions and the support of her father. The act of sharing meals becomes a metaphor for the nourishment of the soul. The chapter is suffused with sensory detail and the bittersweet realization that love endures in the smallest gestures.
Letting Go to Find Ourselves
Recognizing that their relationship has become a crutch, Starlet and Milo agree to part ways—temporarily—to focus on their own healing. The decision is agonizing but necessary. Both embark on journeys of self-discovery: Starlet reevaluates her career and identity, while Milo confronts his depression and learns to accept help. Their love, though put on hold, becomes a source of strength rather than codependency. The chapter is about the paradox of letting go in order to hold on.
The Return of Spring
As winter gives way to spring, both Starlet and Milo emerge from their respective trials with new clarity and purpose. A grand gesture—a rebuilt bicycle, a shared sunrise—reunites them. Their families, once sources of pain, become sources of support. The obstacles that once seemed insurmountable are now part of their shared story. The chapter is a celebration of resilience, forgiveness, and the courage to choose love again.
More, More, More
Starlet and Milo, now free to be together, embark on a new adventure—traveling, teaching, and loving without reservation. Their story, once defined by loss and longing, is now a testament to the power of vulnerability and the beauty of imperfection. The epilogue, set at their sunrise wedding, is a culmination of all they have learned: that love is not about avoiding pain, but about embracing it, growing through it, and always wanting more—more life, more love, more sunrises.
Characters
Starlet Evans
Starlet is a biracial young woman whose life is shaped by the early loss of her Italian mother. Raised to be a "good girl," she clings to routines, academic excellence, and a vision-board future. Her mother's death leaves her adrift, her perfectionism both a shield and a prison. Starlet's journey is one of breaking free from inherited expectations and learning to live—and love—on her own terms. Her relationship with Milo is both a catalyst for growth and a mirror for her own wounds. She is compassionate, loyal, and deeply sensitive, but must learn to prioritize her own needs and desires. Her arc is one of self-discovery, as she moves from living for others to living for herself.
Milo Corti
Milo is a nineteen-year-old high school senior, haunted by the death of his mother and the emotional absence of his alcoholic father. His reputation as a "manwhore" masks profound loneliness and depression. Milo uses sex, substances, and sarcasm to numb his pain, but beneath the armor is a boy desperate for connection. His relationship with Starlet is transformative, forcing him to confront his grief and his fear of vulnerability. Milo's diagnosis of impending blindness adds another layer of existential dread, but also becomes a crucible for growth. He is fiercely loyal, surprisingly gentle, and ultimately courageous in his willingness to heal.
Whitney
Whitney is Starlet's best friend and roommate, a sharp-tongued, fiercely loyal confidante. She provides both comic relief and tough love, challenging Starlet's self-sabotage while supporting her through heartbreak. Whitney's own worldview is shaped by skepticism about men and a commitment to female solidarity. She is the anchor that keeps Starlet grounded, even when she disagrees with her choices. Her presence highlights the importance of chosen family and the power of honest friendship.
Jacob (Starlet's Father)
Jacob is Starlet's Black father, owner of a tattoo parlor and a man marked by both loss and resilience. His love for his late wife and daughter is unwavering, though he struggles to express it in traditional ways. Jacob's journey is one of learning to let go and trust his daughter's choices, even when they scare him. He becomes a surrogate father figure for Milo, offering wisdom and support when it's most needed. His character embodies the theme of imperfect parenting and the possibility of healing across generations.
Milo's Father (Jacob Corti)
Milo's father is a man undone by grief, turning to alcohol to numb the pain of losing his wife. His relationship with Milo is fraught with anger, disappointment, and mutual misunderstanding. Over the course of the story, he hits rock bottom but eventually seeks help, allowing for a tentative reconciliation with his son. His arc is a sobering look at the long shadow of loss and the difficulty of breaking cycles of pain.
Weston (Principal Gallo)
Weston is Milo's uncle and the high school principal, caught between his professional duties and familial love. He is both a disciplinarian and a source of support, struggling to balance the needs of his students with the complexities of his own grief for his sister. Weston's evolution from antagonist to ally is a testament to the power of empathy and the importance of second chances.
Henry and Bobby
Henry, an older blind man, and Bobby, his precocious step-grandson, are members of Milo's support group. They provide comic relief, hard truths, and a sense of community for Milo as he navigates his diagnosis. Their banter and wisdom help Milo see that he is not alone, and that life with disability can still be rich and meaningful.
Whitney's Role Expanded
Whitney's skepticism and humor serve as a counterpoint to Starlet's earnestness. She is the voice of reason, but also the one who pushes Starlet to take risks. Her own journey is less central but provides a necessary balance, reminding Starlet (and the reader) that not all love stories are the same, and that friendship can be as transformative as romance.
Starlet's Mother (Rosa)
Though deceased, Rosa's influence permeates the narrative through her letters, recipes, and the memory of her love. She represents the ideal of unconditional love and the pain of its loss. Her legacy is both a comfort and a burden for Starlet, who must learn to honor her mother without being defined by her absence.
Milo's Mother (Ana)
Ana's death is the inciting trauma for Milo, and her presence lingers in his rituals, memories, and the letter she leaves for his graduation. She is the standard by which Milo measures love and loss, and her wisdom (especially through her recipe box) becomes a source of healing for both Milo and Starlet.
Plot Devices
Dual Narration and Alternating Perspectives
The novel alternates between Starlet's and Milo's points of view, allowing readers to inhabit both sides of the central relationship. This structure deepens empathy and highlights the ways grief, love, and growth are experienced differently but can lead to shared understanding. The dual narration also creates dramatic irony, as the reader often knows more than the characters, heightening tension and anticipation.
Letters and Recipe Cards
The letters from Starlet's and Milo's mothers, along with the recipe box, serve as physical manifestations of love, loss, and legacy. They provide comfort, guidance, and a sense of continuity, anchoring the characters in their histories while propelling them forward. These artifacts are used for foreshadowing, emotional catharsis, and as catalysts for key decisions.
Forbidden Romance and Power Dynamics
The student-teacher relationship is a central plot device, raising the stakes and complicating the characters' choices. The secrecy and risk heighten the emotional intensity, while also forcing both characters to confront their own boundaries and values. The power imbalance is explored with nuance, never shying away from the ethical dilemmas involved.
Grief as Character and Catalyst
Grief is not just a theme but an active force in the narrative, shaping every decision and relationship. The story uses anniversaries, rituals, and breakdowns to externalize internal pain, making the process of mourning visible and communal. Grief is both the antagonist and the path to growth, driving the characters toward each other and, ultimately, toward themselves.
Symbolism of Seasons and Sunrises
The changing seasons mirror the characters' emotional states, with winter representing the coldness of loss and spring the possibility of renewal. Sunrises are a recurring motif, symbolizing the promise of new beginnings and the enduring presence of lost loved ones. The final sunrise wedding is the culmination of this symbolism, uniting past and future in a moment of transcendence.
Support Groups and Found Family
Both Starlet and Milo find solace not just in each other but in the communities they build—friends, family, support groups. These relationships provide perspective, challenge, and unconditional acceptance, reinforcing the idea that healing is a collective endeavor. The found family trope is used to counterbalance the pain of biological loss.
Self-Discovery Through Separation
The decision to separate in order to heal is a key plot device, subverting the idea that love alone is enough. Both characters must confront their own wounds and desires before they can truly be together. This device allows for character growth, delayed gratification, and a more mature, sustainable reunion.
Analysis
Brittainy C. Cherry's The Coldest Winter is a contemporary romance that transcends genre conventions by weaving together themes of grief, healing, and the messy, nonlinear path to self-acceptance. At its core, the novel is about two young people—Starlet and Milo—who are forced to confront the coldest winters of their lives: the loss of their mothers, the collapse of their families, and the shattering of their carefully constructed identities. Through alternating perspectives, Cherry explores the ways trauma shapes us, the dangers of perfectionism and self-sabotage, and the redemptive power of vulnerability. The forbidden romance at the heart of the story is not just a source of tension but a crucible for growth, forcing both characters to reckon with their own needs, boundaries, and desires. The use of letters, recipes, and ritual grounds the narrative in tangible acts of remembrance, while the motif of sunrises offers hope without denying the reality of pain. Ultimately, the novel argues that healing is not about erasing grief but about learning to live alongside it, to find beauty in brokenness, and to choose love—even when it means risking more loss. The lesson is clear: everything's gonna work out fine, not because life is easy, but because we are capable of more—more love, more growth, more life—than we ever imagined.
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