Max Monroe’s When I Should’ve Stayed serves as the emotionally charged second installment in the Red Bridge series, delivering a gut-wrenching exploration of love, loss, and the devastating consequences of timing. Following the foundation laid in What I Should’ve Said, this novel plunges readers into the complex aftermath of Josie and Clay’s tumultuous relationship, weaving together themes of grief, hope, and the resilience of the human heart.
A Story That Cuts Deep
The narrative structure of When I Should’ve Stayed is brilliantly crafted, alternating between “Before the Moment” and “After the Moment” chapters that slowly reveal the catastrophic event that tore Josie and Clay apart. This technique creates an almost unbearable tension as readers piece together the fragments of their love story while watching their present-day struggles unfold.
Josie Ellis emerges as a character of remarkable complexity. Her journey from the confident, sassy woman who once caught cheaters at Clay’s bar to someone drowning in grief and making desperate decisions feels authentic and heartbreaking. The authors masterfully portray her internal struggle between love and self-preservation, making her decision to leave Clay—and the shocking revelation about their divorce papers—feel both devastating and understandable.
Clay Harris, the charming bar owner from New York who found his home in Red Bridge, embodies the archetype of the devoted husband who refuses to give up. His admission that he never signed the divorce papers might seem manipulative on the surface, but Monroe’s nuanced characterization reveals a man desperate to hold onto the only good thing in his life. His vulnerability, especially in scenes involving Summer Bishop, showcases a depth that transcends typical romance novel male leads.
The Heart of Red Bridge: Community and Connection
One of the novel’s greatest strengths lies in its portrayal of Red Bridge as a living, breathing community. The town isn’t merely a backdrop; it’s an integral character that shapes every interaction and decision. From Eileen Martin’s gossipy newspaper reports to the way the entire town rallies around Bennett and Summer, Monroe creates a sense of authentic small-town interconnectedness that feels both comforting and suffocating.
The supporting cast shines particularly bright in this installment. Bennett Bishop’s journey as a single father caring for his terminally ill daughter Summer adds layers of emotional depth that elevate the entire narrative. His relationship with Norah Ellis (Josie’s sister) provides a parallel love story that demonstrates how grief can both destroy and heal relationships.
Summer Bishop: The Catalyst for Everything
Perhaps the most powerful element of When I Should’ve Stayed is its unflinching portrayal of child illness and loss through Summer Bishop’s story. The seven-year-old with osteogenesis imperfecta (brittle bone disease) serves as both the heart of the community and the catalyst for Josie and Clay’s eventual breakdown. Monroe handles this sensitive subject matter with remarkable grace, never exploiting Summer’s condition for cheap emotional manipulation.
The scene where Summer requests the fake wedding ceremony, bringing Josie and Clay together one last time, is simultaneously beautiful and devastating. It demonstrates how children can see love more clearly than adults, cutting through the complicated emotions and circumstances that keep people apart. Summer’s death serves as the emotional climax that forces every character to confront their deepest fears and truths.
Writing Style and Emotional Resonance
Monroe’s writing style in When I Should’ve Stayed feels more mature and confident than in the series opener. The dual timeline structure allows for sophisticated storytelling that gradually reveals information while maintaining emotional intensity. The authors excel at writing authentic dialogue that captures the unique voice of each character, from Clay’s determined declarations of love to Josie’s sharp-tongued deflections.
The intimate scenes between Josie and Clay crackle with both passion and pain, reflecting their complicated emotional state. Monroe doesn’t shy away from the messiness of grief and how it affects physical intimacy, creating realistic portrayals of how trauma impacts relationships.
Critical Analysis: Where the Story Stumbles
While When I Should’ve Stayed succeeds as an emotional powerhouse, it occasionally stumbles under the weight of its own ambitions. The revelation that Clay never signed the divorce papers, while dramatic, feels somewhat contrived and undermines Josie’s agency in their separation. This plot device, though effective for creating conflict, borders on problematic as it essentially traps Josie in a marriage she believed she had legally ended.
The pacing occasionally suffers from the dual timeline structure, with some “Before the Moment” chapters feeling repetitive in their setup of Josie and Clay’s happiness. The authors sometimes over-explain emotional states that could be more effectively conveyed through action and dialogue.
Additionally, while the small-town setting is generally well-developed, some of the secondary characters feel more like plot devices than fully realized individuals. The town’s collective response to tragedy sometimes feels too uniformly supportive, lacking the realistic complexity that would make Red Bridge feel truly authentic.
Themes That Resonate
When I Should’ve Stayed explores several profound themes that elevate it beyond typical romance fiction:
- The Weight of Grief: The novel doesn’t shy away from showing how loss can fundamentally change people, affecting their ability to trust, love, and hope.
- Community vs. Individual Needs: The tension between what the community expects and what individuals need for their own healing creates compelling conflict throughout the story.
- The Complexity of Love: Monroe demonstrates that love isn’t always enough to overcome circumstances, trauma, and personal limitations.
- Timing and Regret: The title itself speaks to the central theme of missed opportunities and the weight of decisions we make in moments of crisis.
The Red Bridge Series Evolution
Compared to What I Should’ve Said, this second installment shows significant growth in emotional maturity and narrative sophistication. Where the first book established the world and characters, When I Should’ve Stayed deepens our understanding of what it means to love and lose in a small community where everyone’s business is public knowledge.
The series progression suggests that Monroe is building toward something larger than individual love stories—they’re creating a tapestry of interconnected lives and loves that reflect the reality of small-town existence.
Final Verdict: A Powerful Addition to Contemporary Romance
When I Should’ve Stayed succeeds as both a standalone emotional journey and a worthy continuation of the Red Bridge series. Monroe’s willingness to tackle difficult subjects like child illness, death, and the long-term effects of trauma on relationships sets this novel apart from typical romance fare.
The book’s exploration of how grief can simultaneously destroy and strengthen relationships feels authentic and necessary in a genre that often glosses over life’s harsher realities. While some plot devices feel heavy-handed, the emotional truth at the story’s core more than compensates for these minor flaws.
For readers who enjoyed the first book, When I Should’ve Stayed provides the emotional payoff and character development that makes the series worth following. For newcomers to the series, this book offers enough context to stand alone while encouraging readers to seek out the full Red Bridge experience.
Recommendations for Similar Reads
If When I Should’ve Stayed resonated with you, consider these similar titles that explore love, loss, and small-town dynamics:
- “The Light We Lost” by Jill Santopolo – For readers who appreciate complex love stories complicated by timing and circumstances
- “Beach Read” by Emily Henry – Another small-town romance that deals with grief and second chances
- “The Seven Husbands of Evelyn Hugo” by Taylor Jenkins Reid – For those who enjoy stories about complicated relationships and the weight of secrets
- “It Ends with Us” by Colleen Hoover – Similar themes of love, loss, and difficult choices
- “The Hating Game” by Sally Thorne – For readers who enjoy the enemies-to-lovers tension that Monroe writes so well
When I Should’ve Stayed earns its place as a compelling example of contemporary romance that doesn’t shy away from life’s complexities. It’s a book that will stay with readers long after the final page, prompting reflection on the nature of love, loss, and the courage required to fight for what matters most.
Monroe has crafted a story that honors both the joy and pain of loving deeply, creating characters who feel real enough to break your heart and a community that feels like home. For readers willing to embark on an emotional journey that doesn’t promise easy answers, When I Should’ve Stayed delivers an unforgettable experience that justifies its place in any romance lover’s library.
