Max Monroe’s “When I Should’ve Stayed” is the emotionally charged second installment in the Red Bridge series, following the tumultuous relationship between Clay Harris and Josie Ellis. This novel doesn’t merely continue their story—it dissects it with surgical precision, exposing the raw wounds of loss, the complexity of grief, and the transformative power of unconditional love.
The Heart of Red Bridge
The small town of Red Bridge serves as more than just a backdrop; it’s a character in its own right, with its gossip-hungry residents, close-knit community dynamics, and the kind of intimacy that makes secrets impossible to keep. Monroe expertly weaves this setting into the narrative, creating a world where every gesture is noticed, every relationship scrutinized, and every heartbreak becomes communal property.
Clay Harris returns as the passionate bartender whose love for Josie burns with an intensity that borders on obsession. His character development reveals layers of vulnerability beneath his seemingly confident exterior. The revelation that he never signed their divorce papers isn’t just a plot twist—it’s a manifestation of his inability to let go, his fundamental belief that their love story isn’t finished.
Josie Ellis emerges as a complex protagonist wrestling with trauma that runs deeper than surface-level marital problems. Her journey through grief, guilt, and the slow process of healing resonates with authenticity. Monroe doesn’t shy away from the messiness of emotional recovery, presenting Josie as a woman who must learn to forgive herself before she can love again.
The Shadow of Summer Bishop
Perhaps the most compelling aspect of this narrative is how the tragic loss of Summer Bishop—Bennett’s daughter who suffered from Osteogenesis Imperfecta—becomes the catalyst for both destruction and healing. Summer’s death doesn’t just provide background drama; it forces every character to confront their own mortality, their capacity for love, and their understanding of what truly matters.
The way Monroe handles Summer’s illness and death demonstrates remarkable sensitivity. Rather than exploiting childhood illness for emotional manipulation, the author presents it as a profound life experience that shapes every adult character’s perspective on love, loss, and the preciousness of time.
Dual Timeline Mastery
Monroe’s decision to structure the novel with “Before the Moment” and “After the Moment” sections creates a literary tension that drives the entire narrative. The “Before” sections reveal the foundation of Clay and Josie’s relationship—their courtship, elopement, and the tragic accident that changed everything. The “After” sections show the aftermath of their separation and the slow, painful process of finding their way back to each other.
This structure allows readers to understand the depth of their connection while simultaneously experiencing the pain of their separation. It’s a storytelling technique that enhances emotional investment, making every small gesture between them feel weighted with history and possibility.
The Weight of Unspoken Truths
One of the novel’s greatest strengths lies in its exploration of how silence can be more destructive than any argument. Clay’s decision to hide their uncompleted divorce papers and Josie’s inability to share her deepest trauma create a chasm between them that widens with each passing day. Monroe demonstrates how good intentions can lead to devastating consequences when communication breaks down.
The pregnancy loss that haunts Josie throughout the novel is handled with exceptional care. Rather than treating it as a plot device, Monroe presents it as a fundamental part of Josie’s identity—something that shaped her understanding of love, loss, and her own worthiness of happiness. The way this trauma affects her relationship with her sister Norah’s pregnancy adds another layer of complexity to her character development.
Supporting Characters That Shine
The residents of Red Bridge aren’t just background players; they’re fully realized individuals with their own stories, motivations, and roles in the central romance. Bennett Bishop’s grief over Summer’s death parallels Clay and Josie’s relationship struggles, while Norah’s pregnancy and relationship with Bennett provides hope and renewal in the face of loss.
Breezy, Bennett’s sister, emerges as a particularly compelling supporting character whose own journey of healing adds depth to the narrative. Her relationship with the community and her role in bringing people together demonstrates Monroe’s skill at creating interconnected storylines that feel organic rather than forced.
The Bar as Sacred Space
Clay’s bar, The Country Club, functions as a central meeting place where relationships are forged, secrets are shared, and healing begins. Monroe uses this setting masterfully, creating scenes that feel both intimate and communal. The bar becomes a metaphor for Clay himself—a place where people come to forget their troubles, find comfort, and sometimes discover unexpected connections.
The Halloween scene where Josie appears in a Snow White costume, referencing Summer’s coloring book drawing, demonstrates Monroe’s ability to weave seemingly small details into significant emotional moments. These connections between past and present give the story depth and resonance.
Writing Style and Emotional Resonance
Monroe’s prose balances contemporary romance conventions with literary depth. The dialogue feels natural and specific to each character, while the internal monologues reveal emotional truths without becoming overly introspective. The pacing allows for both passionate moments and quiet reflection, creating a rhythm that mirrors the ups and downs of real relationships.
The author’s handling of grief is particularly noteworthy. Rather than treating it as something to be overcome, Monroe presents it as something to be integrated into life. The characters don’t “get over” their losses; they learn to carry them while still remaining open to new experiences of love and joy.
Areas for Improvement
While “When I Should’ve Stayed” succeeds in most areas, there are moments where the dramatic tension feels slightly manufactured. Clay’s decision to reveal their marital status during a fake wedding ceremony, while emotionally satisfying, stretches credibility somewhat. Additionally, some of the townspeople’s dialogue occasionally veers into caricature territory, though this is more noticeable in minor characters than in the main cast.
The novel’s length sometimes works against it, with certain emotional beats repeated when they could be more efficiently conveyed. However, this thoroughness also allows for deep character development that might be impossible in a shorter work.
The Red Bridge Series Connection
Readers who enjoyed “What I Should’ve Said” will find this sequel both satisfying and heartbreaking. Monroe successfully deepens the world-building while exploring new emotional territory. The series benefits from its interconnected character relationships, with each book enhancing the others through shared history and overlapping storylines.
For newcomers to the series, “When I Should’ve Stayed” provides enough context to be understood as a standalone work, though reading the first book certainly enhances the experience.
The Verdict
“When I Should’ve Stayed” is a romance that earns its emotional impact through careful character development, authentic dialogue, and a willingness to explore difficult themes. Monroe doesn’t offer easy answers or quick fixes; instead, the novel presents love as something that requires courage, patience, and the willingness to be vulnerable even after being hurt.
This is a story about second chances, but not the kind that come easily. Clay and Josie must work for their happiness, confronting their past mistakes and finding ways to honor their grief while remaining open to joy. The result is a romance that feels both deeply satisfying and emotionally honest.
For Readers Who Enjoyed
If you loved “When I Should’ve Stayed,” consider these similar titles:
- “The Hating Game” by Sally Thorne – For enemies-to-lovers tension with emotional depth
- “Beach Read” by Emily Henry – For small-town romance with serious themes
- “The Seven Husbands of Evelyn Hugo” by Taylor Jenkins Reid – For complex relationships and secrets
- “It Ends with Us” by Colleen Hoover – For emotionally challenging romance
- “The Kiss Quotient” by Helen Hoang – For characters dealing with personal trauma
Final Thoughts
“When I Should’ve Stayed” succeeds as both a romance and a meditation on loss, healing, and the courage required to love fully. Monroe has created characters who feel real enough to care about and a story that lingers long after the final page. While it deals with heavy themes, the novel ultimately affirms the power of love to heal even the deepest wounds.
This is contemporary romance at its finest—emotionally intelligent, character-driven, and unafraid to explore the darker corners of human experience while still delivering the satisfaction readers expect from the genre. For those willing to embark on an emotional journey, “When I Should’ve Stayed” offers rich rewards.