The Art of Starting Over Summary, Characters and Themes

The Art of Starting Over by Heidi McLaughlin is a contemporary romance that explores the fragility of trust, the sting of betrayal, and the quiet strength it takes to begin again.

Alternating between the perspectives of Devorah, a woman reeling from the collapse of her marriage, and Hayden, a widower returning to his hometown with his young son, the story unfolds in the quaint coastal town of Oyster Bay. As both characters work to rebuild their lives, they discover that healing often comes in unexpected forms—and that love, even after deep wounds, can still find its way back into the light.

Summary

The story begins with Devorah, a successful woman living in Chicago, whose world is upended when she watches a shocking social media video: her best friend Ester confessing to an affair with Devorah’s husband, Chad.

Racing home, Devorah finds the truth confirmed—Ester and Chad are together, unapologetic, and in love.

The betrayal by two of the people she trusted most sends Devorah into a tailspin.

She decides to leave Chicago with her teenage daughter, Maren, for the small coastal town of Oyster Bay, where her father and brother live.

Meanwhile, Hayden McKenna, a widower raising his young son Conor, also returns to Oyster Bay, seeking solace after the death of his wife Sofia.

Plagued by guilt and grief, Hayden plans to stay with his parents temporarily while he figures out his next steps.

Oyster Bay holds memories of his youth, including a romantic spark that once existed between him and Devorah back in high school.

That ember has long been buried beneath the separate paths they both took.

As Devorah and Maren settle into life with her stern but loving father, Sheriff Crow, and her brother Colt, they begin adapting to the rhythms of small-town life.

Maren bonds with her grandfather and their new puppy, Cordelia, while Devorah quietly struggles with emotional wreckage.

At the same time, Hayden is doing his best to be a good father to Conor, whose grief sometimes shows itself through behavioral issues.

Hayden reconnects with Colt, now a successful local business owner, and the community that once shaped him.

When Devorah and Hayden cross paths, old memories begin to stir.

Though both are hesitant and emotionally scarred, they find unexpected comfort in each other’s presence.

As their interactions grow more frequent, so does the mutual understanding between them.

Their parallel experiences of loss—Devorah’s betrayal and Hayden’s bereavement—create a unique bond that slowly grows into something deeper.

A storm causes a power outage one evening, forcing Devorah and Hayden into an emotionally intimate conversation that leads to their first kiss.

As they navigate the beginnings of a relationship, obstacles arise.

Colt discovers their budding romance and confronts Hayden, wary of anyone hurting his sister again.

After a heartfelt conversation, he gives his reluctant blessing, recognizing the sincerity of Hayden’s feelings.

Devorah receives final divorce papers from Chad, an emotional moment that ultimately grants her closure.

At the same time, Hayden opens up to her about the guilt he carries over Sofia’s death—an accident he believes he could have prevented.

In sharing their wounds, they begin to truly heal.

Maren flourishes in Oyster Bay, excelling at school, making new friends, and growing close to both her grandfather and Conor.

Devorah, too, becomes more grounded.

Her relationship with her father softens as he begins to express pride in her strength.

Hayden, now emotionally freer, takes Devorah on a nostalgic date, where they share laughter, vulnerability, and the possibility of a shared future.

In the final chapters, Hayden asks Conor for his thoughts about building a life with Devorah and Maren.

Conor’s enthusiastic support clears the path for Hayden to move forward.

Devorah and Hayden commit to each other—not as a rebound or a distraction from past pain, but as a conscious choice for something real and lasting.

The epilogue paints a picture of a blended family thriving in Oyster Bay.

Hayden is planning to propose, and both families are adjusting with warmth and love.

The Art of Starting Over ends not with dramatic fireworks but with quiet hope—a testament to the resilience of the human heart and the beauty of second chances.

Characters

Devorah

Devorah is a complex character whose emotional journey is central to The Art of Starting Over. At the beginning of the story, she is devastated by betrayal, having discovered that her husband, Chad, is not only cheating on her but has fallen in love with her best friend, Ester.

This traumatic realization sets the stage for Devorah’s personal evolution. Initially, she is overwhelmed by grief and shock, but over time, she finds strength in her new surroundings and routines in Oyster Bay.

The support of her daughter, Maren, and the solace she finds in reconnecting with her father and brother, helps her rediscover her resilience. While Devorah’s emotional wounds are deep, she slowly begins to heal by allowing herself to feel hope again.

Her eventual connection with Hayden marks the beginning of her ability to trust and open her heart to love once more, but it’s a process laden with the fear of repeating past mistakes. Her growth throughout the novel is a testament to her inner strength, showing that healing from betrayal is not linear but requires facing past wounds and allowing oneself to be vulnerable in the present.

Hayden

Hayden, a widower, arrives in Oyster Bay with his young son, Conor, seeking a fresh start after the tragic death of his wife, Sofia. While he carries immense grief and guilt over his wife’s passing, he is determined to provide a stable and loving environment for Conor.

Hayden’s story arc is marked by his struggle to balance his emotions and his fatherly responsibilities. Despite the heavy sorrow he feels over Sofia’s death, Hayden’s connection to his roots in Oyster Bay offers him some comfort, and he finds solace in the familiarity of old places and people.

His chance reunion with Devorah awakens long-suppressed feelings, as the two shared a brief romantic moment in high school that never materialized due to the timing and Devorah’s marriage to Chad. Throughout the novel, Hayden’s emotional evolution mirrors Devorah’s as they both confront their pasts and form a bond built on shared grief.

His eventual confession of long-held feelings for Devorah is a pivotal moment, as it marks the beginning of their healing journey together. Despite his fears and hesitations, Hayden opens himself to the possibility of love once again, ultimately embracing the future with Devorah by his side.

Maren

Maren is Devorah’s young daughter, and though she is a secondary character, her emotional journey is significant to the narrative. Initially, Maren is as devastated by the betrayal as her mother, particularly since it means the end of her friendship with Ester’s daughter, Rita.

However, as the family relocates to Oyster Bay, Maren begins to find solace in the small-town life, growing closer to her grandfather, Crow, and bonding with a puppy named Cordelia. Her adaptation to this new chapter of their lives is heartwarming and serves as a catalyst for Devorah’s own healing.

Maren’s transformation from a grieving child to a more joyful and optimistic young girl is a symbol of hope and renewal in the story. As she flourishes in her new environment, it becomes clear that she plays an important role in her mother’s ability to move forward and embrace the future.

Chad

Chad, Devorah’s ex-husband, plays a pivotal yet antagonist role in the novel. His affair with Ester and subsequent betrayal of Devorah is the catalyst for the entire narrative. At the beginning of the story, Chad is shown to be cold and unapologetic about his actions.

His confession that he is in love with Ester and plans to leave Devorah for her is devastating for his family. Throughout the story, Chad remains a symbol of betrayal and emotional damage, but his presence is essential in understanding Devorah’s pain and the depth of her emotional turmoil.

While he does not appear frequently, his actions have far-reaching consequences, driving Devorah to leave her life in Chicago and seek refuge in Oyster Bay. His eventual divorce from Devorah provides the closure she needs, allowing her to begin the process of emotional recovery and ultimately make space for a new relationship with Hayden.

Colt

Colt, Devorah’s brother, is a secondary yet supportive character. He initially struggles with the betrayal by his sister’s best friend, Ester, and her husband, Chad. Despite his initial anger and resentment toward them, Colt stands by Devorah, providing emotional support and protection when necessary.

As the owner of a local brewery, Colt reconnects with Hayden, and their friendship is rekindled, with Colt providing some much-needed wisdom and guidance to Hayden as he navigates his grief and burgeoning feelings for Devorah. Colt’s role in the story is to highlight the importance of family and loyalty, and his eventual approval of Hayden’s relationship with Devorah is a mark of trust and understanding.

His character is a grounding presence, and his relationship with Devorah strengthens as they work through the emotional turmoil surrounding their family’s dynamics.

Themes

The Emotional Architecture of Betrayal and Its Aftermath in Intimate Relationships

The Art of Starting Over talks about the visceral, disorienting impact of betrayal within the closest circles of trust—marriage and friendship. Devorah’s discovery of her husband’s affair with her best friend shatters the foundational pillars of her identity and emotional security.

This betrayal is not only physical but existential. It forces her to reevaluate her worth, her history, and her relational choices.

The novel explores how betrayal fractures more than just the marital bond—it disrupts maternal stability, female friendships, and the sense of safety within one’s own skin. It also shows the long psychological shadow cast by infidelity, with Devorah vacillating between paralysis and fierce independence.

Her journey is not about simply leaving a cheater. It is about rebuilding a sense of self that has been hollowed out by duplicity.

Intergenerational Masculinity, Emotional Suppression, and the Possibility of Redemption

Through the characters of Hayden, Crow, and even Colt, the novel constructs a meditation on what it means to be a man across generations. It explores how emotional expression—or the lack thereof—becomes a learned behavior.

Crow’s stern demeanor and traditional stoicism initially feel emotionally withholding. But as Devorah and he begin to reconnect, his quiet strength transforms into quiet support.

Hayden, meanwhile, is a deeply modern man shaped by loss, fatherhood, and a desire to love again while still honoring the past. He is caught between being a role model for his son and a broken man trying to hold himself together.

The book probes how these men navigate grief, guilt, protectiveness, and vulnerability. It highlights the challenge of doing so when the emotional lexicon handed to them by prior generations lacks fluency for pain.

The Slow Erosion and Tentative Reclamation of Female Agency in the Wake of Domestic Collapse

Devorah’s character arc is fundamentally about reclaiming agency after systemic emotional diminishment. What begins as reaction—fleeing from betrayal—evolves into proactive decision-making.

She reclaims her identity, both within the family and the community. Her agency does not roar into being; it creeps, stumbles, and occasionally retreats.

Yet this incremental progress makes her growth feel deeply authentic. The novel resists the trope of immediate reinvention.

Instead, it portrays empowerment as a fragile, often interrupted process that requires solitude, self-doubt, and small wins. Devorah’s decision to stay in Oyster Bay reflects a layered, intentional reassertion of control over her future.

Spatial and Temporal Nostalgia as Emotional Refuge and Psychological Constraint

Oyster Bay is more than just a setting—it functions as both sanctuary and emotional trigger for Devorah and Hayden. The small town’s nostalgic pull reminds them of a life before betrayal and grief.

It offers a sense of familiarity that both comforts and confines. The temporal elasticity of the town—where the past feels ever-present—serves as both a balm and a barrier.

Hayden finds moments of healing by reconnecting with places that once held joy. But he also contends with the shadows of old mistakes and memories.

Similarly, Devorah is constantly reminded of her youth, her father’s expectations, and the person she used to be. The novel suggests that while physical spaces can be restorative, they can also inhibit growth if one becomes too beholden to what they once meant.

Dual Parenting and the Reconstruction of Familial Identity After Trauma

Both Hayden and Devorah are single parents thrust into emotional triage, not just for themselves but for their children. Their parallel stories are threaded with the challenges of parenting amidst upheaval.

They must learn how to nurture while breaking, how to instill trust while navigating betrayal or grief. Maren and Conor reflect their parents’ pain but also become sources of unexpected resilience and perspective.

The narrative doesn’t portray parenting as redemptive in a sentimental way. Rather, it shows it as a daily negotiation between fear and hope.

As the families blend, the book explores the complicated work of building a new family unit. It honors the love that came before while daring to imagine something new and whole.

This theme reflects how love, when redistributed across new emotional configurations, can still provide roots and wings.