When I Should’ve Stayed Summary, Characters and Themes
When I Should’ve Stayed by Max Monroe is a contemporary romance set in the small Vermont town of Red Bridge. It follows Josie Ellis and Clay Harris, two complicated people navigating the aftermath of heartbreak, personal loss, and the challenge of moving on.
The story explores themes of love, forgiveness, and growth as Josie and Clay confront their painful past and the possibility of a future together. Both are deeply flawed yet resilient characters who find themselves repeatedly drawn back into each other’s lives despite scars that threaten to keep them apart. The novel balances moments of tender connection with the realities of emotional wounds and family complications.
Summary
The narrative centers on Josie Ellis, a woman who starts the story carrying divorce papers and feeling a painful mix of heartbreak and regret. She is leaving behind a life once filled with hope but now marked by loss.
Josie reflects on the ghosts of her past and the familiar places and faces in Red Bridge, including Clay’s bar, The Country Club. Despite the sorrow and guilt she carries, Josie feels the need to step away and face an uncertain future, marking a turning point in her journey toward maturity.
Clay Harris, the charismatic owner of The Country Club, watches Josie with concern and admiration. He notices her pattern of exposing cheating men at his bar, a crusade that speaks to her fierce independence and desire to protect others from deceit.
Clay’s protective instincts come to the fore when he removes a violent man from the bar, revealing his caring nature beneath a confident exterior. His complicated past from New York contrasts with his growing feelings for Josie, creating a magnetic pull between them.
Their relationship evolves from cautious acquaintances to tentative lovers, filled with humor, flirtation, and emotional depth.
Josie lives with her grandmother, Rose, who supports her through personal and family struggles. Josie’s “hobby” of catching cheaters has made her known in nearby towns, and despite her tough exterior, she grapples with a traumatic childhood marked by loss and a difficult relationship with her manipulative mother.
This backstory adds layers to her character, showing resilience and a desire for honesty and safety in relationships.
A defining moment occurs atop the town’s water tower, Josie’s secret refuge. Here, Josie and Clay share an intimate encounter that deepens their connection.
This scene is a physical and emotional turning point, symbolizing their willingness to confront fears and open up to each other. The story moves forward as Josie fulfills her dream of opening a coffee shop named CAFFEINE, despite financial and emotional challenges.
Clay’s presence in the community and his complicated feelings for Josie stir unresolved tension and hope.
Clay struggles with his own demons and regrets, watching Josie move ahead while wrestling with his desire to be part of her life. His friendship with Bennett Bishop, who faces his own burdens caring for his special needs daughter Summer, adds depth to the story.
Clay and Bennett’s journey into unexpected parenthood brings themes of loyalty and responsibility into focus. Josie acts as a steadying influence in their lives, providing emotional and practical support.
A significant plot point unfolds when Josie is pulled into a fake wedding staged by her sister Norah to fulfill a dying child Summer’s wish to witness a wedding. Josie is shocked to learn that the groom is Clay, her ex-husband.
Initially furious and hurt, Josie eventually agrees to participate, driven by compassion for Summer. The ceremony reveals a startling truth: Clay never signed their final divorce papers, meaning they are still legally married.
This revelation triggers a painful confrontation, leading Josie to seek refuge in her coffee shop and open up about her unresolved grief, including a miscarriage and the death of her grandmother.
Further conflict arises when Bennett is arrested following a violent confrontation involving Norah’s abusive ex and Josie’s manipulative mother. Norah presents evidence that shifts power away from those trying to sabotage them.
Summer’s biological mother attempts to re-enter the picture but is blocked legally and emotionally. The focus returns to Summer as her health declines rapidly.
Josie and Clay, united by shared grief, spend Summer’s final moments together. A simple coloring book page with the words “Clay loves Josie” becomes a poignant symbol of their enduring connection.
After Summer’s death, the community mourns, and Josie and Clay find solace in each other’s presence.
The story also traces the rebuilding of Josie and Clay’s relationship. On New Year’s Eve, Clay declares his love for Josie in front of the whole town, signaling his commitment.
Their romance develops over seasonal celebrations, such as an Easter egg hunt and the Fourth of July fireworks, where moments of joy and flirtation rekindle their bond. Josie finally reveals the painful secret that led to their divorce: a miscarriage and medical complications that left her unable to have children.
Clay responds with understanding and recommits to her.
At a wedding for Norah and Bennett, Josie initially wants to stay apart, but after an emotional exchange, she returns and accepts Clay’s renewed proposal, symbolized by a water tower–shaped ring he kept for years. They remarry surrounded by family and friends, hopeful despite past hardships.
The couple begins building a new life together, purchasing land and discussing adoption, signaling a fresh start.
Throughout the book, the small-town setting of Red Bridge and its close-knit community play a crucial role. Traditions and events ground the characters, giving a sense of belonging and continuity even as they face personal upheavals.
The characters’ stories—especially Josie, Clay, Bennett, and Norah—highlight themes of love, forgiveness, family trauma, and the strength it takes to heal and move forward.
In the end, When I Should’ve Stayed presents a realistic portrayal of relationships marked by past mistakes, complex emotions, and hope for redemption. Josie and Clay’s journey reveals that while love can cause pain, it can also be the foundation for healing and new beginnings.
Their story is one of endurance and the willingness to face the future together, despite the scars left by their past.
Characters
Josie Ellis
Josie Ellis is a deeply complex character whose journey is marked by resilience, vulnerability, and a fierce independence shaped by a troubled past. Living in the small town of Red Bridge, she carries the weight of painful memories—from a traumatic childhood marked by family loss and emotional neglect to a tumultuous romantic history with Clay Harris.
Josie’s defining trait is her strength in the face of hardship; despite her vulnerability, she has carved out a space for herself, working as a waitress and later opening her own coffee shop, CAFFEINE, symbolizing her desire for renewal and control over her life. Her “hobby” of catching cheaters reveals both her protective nature and the emotional scars that make her wary of trust.
Josie’s relationships with her family, especially her difficult dynamic with her manipulative mother Eleanor and her estranged sister Norah, add layers of emotional complexity, as she grapples with forgiveness and reconciliation. Her evolving relationship with Clay showcases a woman who balances guardedness with the yearning for love and connection, navigating heartbreak, regret, and ultimately hope.
Josie’s story is one of painful personal growth—moving from naivety through heartbreak toward a mature, if cautious, embrace of new beginnings.
Clay Harris
Clay Harris is a charismatic yet troubled figure whose life contrasts sharply with Josie’s but ultimately complements hers. A former playboy from New York who has settled into the rhythms of small-town life by running The Country Club bar, Clay carries his own emotional burdens, including a complicated past with wealthy but emotionally distant parents.
His protective instincts surface clearly in his interactions with Josie, whom he admires for her strength and independence even as he worries about the risks she takes in exposing cheating men. Clay’s affection grows deeper as the story progresses, moving from playful flirtation to a heartfelt declaration of love, reflecting his transformation from a carefree, sometimes reckless man to one capable of genuine commitment.
His deep friendship with Bennett Bishop, forged through shared responsibilities in caring for Bennett’s special needs daughter, Summer, reveals Clay’s capacity for loyalty, growth, and tenderness. His struggles with jealousy, heartbreak, and pride underscore a man learning to reconcile his past mistakes with the hope for a meaningful future with Josie.
Clay’s presence is both grounding and transformative in Josie’s life, embodying themes of love’s complexities and the possibility of healing.
Bennett Bishop
Bennett Bishop is a pivotal supporting character whose life intersects deeply with Clay and Josie’s, adding a layer of responsibility and emotional weight to the narrative. Once part of a reckless, privileged past alongside Clay, Bennett has undergone a significant transformation driven by his role as a devoted father to his special needs daughter, Summer.
This responsibility forces Bennett to confront his shortcomings and grow into a protective, loving parent despite the steep learning curve and the challenges they face. His relationship with Clay is both a source of strength and occasional tension, reflecting the difficulties of transitioning from their past lives to their current realities.
Bennett’s interactions, particularly in moments of crisis involving his family, highlight themes of loyalty, resilience, and the enduring power of friendship. His character adds depth to the community dynamic in Red Bridge, grounding the story’s emotional core in the realities of caregiving and sacrifice.
Norah
Norah, Josie’s sister, is a complex character whose sudden reappearance in Red Bridge introduces tension and the possibility of reconciliation. Their relationship is fraught with resentment and unresolved trauma stemming from a troubled family history, especially the manipulative and cruel behavior of their mother, Eleanor.
Norah’s motivations—partly rooted in seeking refuge and partly in wanting to mend broken family ties—create emotional turmoil for Josie, forcing her to confront past wounds she had tried to suppress. Norah’s involvement in the staged wedding for Summer’s dying wish brings additional complications, emotionally dragging Josie into a situation tied to her painful history with Clay.
Despite the tension and distrust, Norah’s character represents the complicated nature of family bonds, highlighting themes of forgiveness, loyalty, and the struggle to heal damaged relationships.
Summer
Summer, Bennett’s daughter, serves as a poignant symbol of innocence, hope, and the transformative power of love within the narrative. Born with Osteogenesis Imperfecta Type III, her fragile condition places her at the center of the story’s emotional landscape.
Summer’s presence compels the adult characters to grow, take responsibility, and confront their vulnerabilities. The fake wedding staged to fulfill her dying wish becomes a catalyst for reconciliation and emotional revelation, uniting characters across their personal conflicts.
Summer’s ultimate passing marks a deeply sorrowful yet unifying moment for the community and particularly for Josie and Clay, underscoring themes of love, loss, and the preciousness of time. Her character’s impact extends beyond her life, symbolizing new beginnings and the enduring connections forged through shared grief.
Rose
Rose, Josie’s grandmother, provides a warm and grounding influence amid the tumultuous events in Josie’s life. Her spirited personality and steadfast support create a safe space for Josie, offering emotional stability and familial love that contrast sharply with Josie’s strained relationships with her mother and sister.
Rose’s presence and involvement in Josie’s candle business further root Josie in the community of Red Bridge, emphasizing themes of tradition, family strength, and the quiet resilience found in intergenerational bonds. Through Rose, the narrative highlights the importance of nurturing connections that sustain individuals through hardship and change.
Themes
The Complexity of Love and Relationships
Love in When I Should’ve Stayed is portrayed not as a simple, idealized feeling but as a multifaceted, often contradictory force that shapes the lives of Josie and Clay profoundly. Their relationship is filled with moments of passion, regret, pain, and hope, revealing how love can simultaneously heal and hurt.
The story captures the tension between vulnerability and independence, showing Josie’s struggle to protect herself after past betrayals and losses while still yearning for genuine connection. Clay’s evolving affection and devotion contrast with his own past recklessness, illustrating how love demands growth and sacrifice.
The narrative explores how love does not erase pain but requires confronting difficult truths and forgiving both oneself and others. Their journey from estrangement through reconciliation and potential new beginnings highlights love’s endurance beyond heartbreak and the work needed to rebuild trust.
The emotional layers in their relationship emphasize that love is rarely straightforward—it involves navigating misunderstandings, hidden fears, and personal scars. This theme underscores the idea that love’s power lies not just in romance but in the courage to face imperfection, communicate honestly, and embrace change.
Personal Growth and Healing
Personal transformation is central to the characters’ arcs, especially Josie’s. Her evolution from someone haunted by past trauma, loss, and family dysfunction to a woman who dares to hope and dream again forms a significant emotional backbone of the story.
Josie’s journey reflects the complexity of healing, which is neither linear nor easy. She must confront deep-seated pain from childhood abuse, family estrangement, miscarriage, and heartbreak, learning to forgive herself and others.
The act of leaving and returning—symbolized by her leaving the town and later opening her own coffee shop—demonstrates her growth toward autonomy and self-acceptance. Clay’s transformation also plays a vital role, as he moves from a careless, privileged youth to a responsible, caring partner and caregiver, showing that maturity often arises from taking responsibility for others and facing one’s vulnerabilities.
The characters’ healing is portrayed realistically, with setbacks and doubts, reinforcing that growth is an ongoing process shaped by love, community support, and personal determination. This theme explores how confronting the past and embracing change are essential for reclaiming one’s life and future.
The Impact of Family and Community
Family dynamics and the small-town community setting shape much of the narrative’s emotional texture. Josie’s complicated relationship with her mother and sister exposes how familial wounds and betrayals leave lasting marks.
The reappearance of Josie’s estranged sister Norah forces painful reckonings with past trauma and the possibility of forgiveness, highlighting how family can both wound and offer redemption. The presence of Josie’s grandmother Rose as a source of warmth and stability contrasts with the harshness of Josie’s childhood, showing that family ties are not monolithic but nuanced and varied.
The tight-knit community of Red Bridge acts as both a backdrop and a character itself, influencing events like the fake wedding and communal celebrations. The town’s traditions, festivals, and shared struggles create a sense of belonging and continuity that support the characters through their hardships.
This theme illustrates how the social environment shapes identity and emotional resilience, and how connection—whether familial or communal—can be both a source of conflict and healing. It also emphasizes the importance of loyalty, support, and understanding in overcoming personal and collective challenges.
Coping with Loss and Grief
Loss permeates the narrative on multiple levels, affecting the characters deeply and driving much of their emotional development. Josie’s experience of miscarriage, her grandmother’s death, and the loss of her sister Jezzy are pivotal moments that shape her guarded demeanor and reluctance to fully embrace happiness.
Clay’s regrets and unresolved feelings for Josie also underscore the theme of loss, as does the heartbreaking situation surrounding Summer, the terminally ill child whose final wish sparks the fake wedding and brings the characters together. The story portrays grief as a powerful, often isolating force but also one that can catalyze connection and compassion.
The characters’ struggles to process and express their pain are depicted with raw honesty, showing how grief intertwines with memory, guilt, and hope. Their collective mourning, especially in Summer’s final moments and funeral, becomes a catalyst for reconciliation and renewed bonds.
This theme highlights the necessity of acknowledging sorrow and the possibility of finding solace and meaning amid heartbreak, emphasizing that grief is an integral part of healing and moving forward.
The Challenge of Forgiveness and Reconciliation
Forgiveness emerges as a vital but difficult theme, woven through Josie’s relationship with her family, especially her sister and mother, as well as with Clay. The story shows that forgiveness is not a simple act but a process requiring vulnerability, courage, and time.
Josie’s initial resentment and guardedness stem from deep wounds inflicted by family dysfunction and personal betrayals, making reconciliation painful and fraught with setbacks. Norah’s return challenges Josie to weigh her anger against the possibility of healing fractured bonds.
Similarly, the rekindling of Josie and Clay’s relationship depends on confronting past hurts, misunderstandings, and secrets, such as the miscarriage and the unsigned divorce papers. Forgiveness here is portrayed as a necessary step toward freedom from the past, but one that must be earned and negotiated carefully.
It is not portrayed as unconditional or easy but as a mutual process that allows the characters to rebuild trust and envision a future together. This theme emphasizes that forgiveness does not erase history but transforms it, allowing individuals to move forward with greater understanding and compassion.
The Role of Caregiving and Responsibility
The subplot involving Clay and Bennett caring for Bennett’s special needs daughter Summer adds an important dimension to the story’s exploration of responsibility and love. This role forces two characters once marked by recklessness and privilege to grow into caregivers, highlighting how responsibility can be a powerful agent of personal change.
Their struggle to navigate parenthood without experience reveals the tenderness, frustrations, and humor involved in caregiving. Summer’s fragile condition and limited time inject urgency and emotional weight into the narrative, underscoring themes of sacrifice, devotion, and the fragility of life.
Josie’s involvement in supporting this family dynamic further showcases her nurturing side and her emerging role within the community. This theme expands the idea of love beyond romance to include the deep bonds formed through care and commitment.
It highlights how taking responsibility for others can lead to profound emotional growth and redefines what family and loyalty mean in the face of hardship.