Christmas Eve Collision Course

Caroline Parker, a top Boston divorce attorney, is no fan of Christmas. Her childhood memories are marred by family chaos and heartbreak, and her adult life as a divorce lawyer only reinforces her skepticism about holiday magic. On Christmas Eve, after a grueling day at work and a recent breakup, she stops for coffee, only to run into Hannah Dalton, the estranged wife of her former nemesis at work. This chance encounter, set against the backdrop of a city glittering with forced cheer, is the first domino in a series of events that will upend Caroline's carefully controlled, emotionally guarded life.

Coffee, Chance, and Chemistry

Inside the café, Caroline is stunned to see Hannah working as a barista. Their brief, awkward exchange is loaded with unspoken history—Caroline knows Hannah only as the wife of Michael Dalton, the man who stole her promotion and made her work life hell. Yet, there's an undeniable pull between them, a flicker of chemistry that neither can ignore. Caroline leaves with more than coffee: a cup marked with Hannah's number and a cryptic invitation to call, setting the stage for a slow-burning connection.

Family Dinners and Old Wounds

Caroline's family dinner is a cacophony of teasing, questions about her love life, and the ever-present ache of being the odd one out. Her mother's discovery of Hannah's number on the coffee cup becomes a running joke, but for Caroline, it's a reminder of her isolation and the yearning for something more. The evening underscores her role as the "cool, single aunt," masking her deeper loneliness and desire for connection.

The Number on the Cup

Alone on Christmas night, Caroline debates whether to call Hannah. The number on the cup is both a temptation and a risk—Hannah is newly separated, has a child, and is entangled in the same legal world Caroline inhabits. After days of internal debate and encouragement from her best friend Kris, Caroline finally texts Hannah, unable to resist the mystery and the possibility of something new.

Divorce, Distance, and Discovery

Their first meeting is fraught with misunderstanding—Hannah wants Caroline to represent her in her divorce from Michael, not to date her. Despite the awkwardness, Caroline agrees to take the case pro bono, drawn by both professional challenge and personal intrigue. As they work together, Caroline uncovers the layers of Hannah's unhappy marriage, her fears for her daughter Abbie, and the courage it took to leave. The legal battle becomes a crucible for both women, testing their boundaries and deepening their connection.

Lunches, Law, and Longing

Regular meetings at The Bean Dream café become the heartbeat of their evolving relationship. Caroline is drawn to Hannah's resilience and vulnerability, while Hannah finds solace in Caroline's steadiness and empathy. Their conversations move from legal strategy to personal confessions, and the lines between lawyer and client, friend and something more, begin to blur. Abbie, Hannah's precocious daughter, becomes a bridge between them, and Caroline's role in their lives grows from professional to personal.

Pillow Forts and Parenting

When Hannah's childcare falls through, Caroline steps in, watching Abbie after school and on weekends. Their home becomes a haven of pillow forts, baking disasters, and laughter. Caroline's bond with Abbie cements her place in their family, and her feelings for Hannah intensify. The trio forms an unconventional but loving unit, challenging Caroline's self-imposed moratorium on dating and forcing her to confront what she truly wants.

Boundaries Blurred, Hearts Stirred

As Caroline and Hannah's friendship deepens, so does the undercurrent of attraction. Movie nights, shared meals, and inside jokes create an intimacy that feels both inevitable and forbidden. Both women struggle with their feelings—Caroline out of fear of heartbreak and professional ethics, Hannah out of loyalty to her daughter and her need for independence. The tension simmers, culminating in moments of almost-confession and near-misses that leave both women reeling.

Girl's Weekend Confessions

A girls' weekend with Caroline's friends becomes a turning point. Sharing a bed, late-night conversations, and drunken confessions about sex and longing bring their desires to the surface. The boundaries between them dissolve further, but fear and uncertainty keep them from acting on their feelings. The weekend is a microcosm of their relationship—full of possibility, restraint, and the ache of what could be.

The Almost Kiss Catastrophe

During a late-night baking session, an almost-kiss shatters the unspoken rules they've lived by. Hannah's panic and retreat leave Caroline hurt and confused, forcing her to reevaluate her feelings and her place in Hannah's life. Both women pull back, trying to restore normalcy, but the incident lingers, making it impossible to return to the way things were.

Recovery Plans and Realizations

Caroline attempts to move on, dating casually and spending less time with Hannah and Abbie. Yet, absence only sharpens her longing and makes her realize the depth of her love for both. Meanwhile, Hannah grapples with her own feelings, torn between the safety of routine and the risk of opening her heart. Their separation is a crucible, burning away pretense and leaving only the truth.

Holiday Parties and Hidden Feelings

The holiday season forces both women to confront their feelings. Family gatherings, school concerts, and work parties are charged with unspoken tension. A stolen kiss at Caroline's birthday and a passionate encounter during the first snow finally break the stalemate. The holidays, once a source of dread for Caroline, become a backdrop for transformation and hope.

Thanksgiving Tightropes

Thanksgiving with Caroline's family is both joyful and fraught. Hannah is welcomed, but the weight of secrecy and the fear of disrupting Abbie's stability loom large. The day is a tightrope walk between public affection and private longing, underscoring the risks and rewards of blending their lives.

First Snow, First Surrender

A chance meeting during the season's first snowfall leads to a passionate, public kiss. The physical and emotional barriers between them finally collapse, and both women surrender to the depth of their feelings. The world outside fades away, leaving only the two of them, finally together in every sense.

Drawing Out the Truth

Hannah's sketchbook, filled with drawings of Caroline, becomes a silent testament to her love. When she finally shares it, the truth is undeniable—she has loved Caroline for longer than she realized, in ways words could never capture. The act of sharing her art is an act of trust, and Caroline's response is a promise of unwavering love and partnership.

Trust, Turmoil, and Taking Leaps

Michael's interference and the threat of custody battles force Hannah and Caroline to confront their fears and insecurities. Caroline's protective instincts clash with Hannah's need for autonomy, leading to painful but necessary conversations about trust, boundaries, and what it means to truly support one another. In the crucible of crisis, they choose each other, not out of need, but out of love.

Christmas Morning Magic

On Christmas morning, Caroline wakes to find Hannah waiting for her, ready to take the leap. Surrounded by the warmth of chosen family and the chaos of holiday cheer, they exchange gifts, laughter, and promises. The holiday, once a symbol of loneliness and loss, becomes a celebration of love, resilience, and new beginnings.

Mistletoe and New Beginnings

A final, playful gift from Abbie—a sprig of mistletoe—gives Hannah and Caroline permission to claim their happiness openly. Their kiss, witnessed and cheered by Abbie, is both an ending and a beginning. The story closes on the promise of a life built not on chance, but on choice, trust, and the magic of love found when least expected.

Characters

Caroline Parker

Caroline is a fiercely intelligent, successful divorce attorney whose cynicism about love and the holidays masks a deep longing for belonging and intimacy. Her childhood and professional experiences have made her wary of vulnerability, but beneath her sarcasm and competence lies a heart that aches for family and partnership. Her journey is one of learning to trust, to risk her heart, and to accept that love can be both messy and miraculous. Her relationship with Hannah and Abbie transforms her, revealing her capacity for tenderness, courage, and selfless devotion.

Hannah Dalton

Hannah is a woman emerging from the shadow of an oppressive marriage, determined to reclaim her independence and provide stability for her daughter. Artistic, thoughtful, and quietly strong, she is both cautious and deeply feeling. Her struggle is to balance her need for autonomy with her desire for connection, and to trust that she can love and be loved without losing herself. Her relationship with Caroline is a catalyst for healing, growth, and the rediscovery of joy and passion.

Abbie Dalton

Abbie is Hannah's ten-year-old daughter, wise beyond her years and endlessly curious. She is the glue that binds Caroline and Hannah, her innocence and openness providing both comic relief and emotional depth. Abbie's acceptance and affection for Caroline are instrumental in breaking down barriers and forging a new family.

Michael Dalton

Michael is Hannah's ex-husband and Caroline's former workplace rival. His manipulative, self-serving behavior is a source of conflict and trauma for both women. He represents the forces of patriarchy, privilege, and emotional abuse that Hannah must overcome. His attempts to control Hannah and Abbie's lives are ultimately thwarted by their resilience and Caroline's advocacy.

Kris

Kris is Caroline's best friend, providing comic relief, tough love, and unwavering support. She is the voice of reason and reality, challenging Caroline's self-sabotage and encouraging her to take risks. Her friendship is a touchstone for Caroline, grounding her in moments of doubt and celebration.

Robyn

Robyn is Hannah's close friend and Abbie's babysitter, offering practical help and emotional support. She is a witness to Hannah's transformation and a quiet champion of her happiness. Robyn's presence underscores the importance of chosen family and community.

Caroline's Family (Tricia, Jared, Todd, Brian, etc.)

Caroline's large, boisterous family is both a source of stress and a wellspring of love. Their teasing, traditions, and occasional insensitivity highlight Caroline's sense of otherness, but their eventual acceptance of Hannah and Abbie is a testament to the power of love to expand and redefine family.

The Bean Dream Staff (Jo, Karla, etc.)

The café staff and Hannah's classmates provide a backdrop of everyday life, illustrating the importance of work, routine, and small acts of kindness in the process of healing and connection.

Caroline's Friends (Jess, Lacey, Miranda)

Caroline's college friends are a reminder of her past and a measure of her growth. Their acceptance of Hannah and their role in pivotal moments (like Girl's Weekend) help Caroline see herself through new eyes and embrace change.

Michael's Parents

Michael's parents represent the expectations and judgments of the past. Their interactions with Hannah and Caroline highlight the challenges of breaking free from toxic family dynamics and forging a new path.

Plot Devices

Dual Narrative of Healing and Romance

The novel intertwines the legal drama of Hannah's divorce with the slow-burn romance between her and Caroline. Each woman's personal growth is mirrored in the evolution of their relationship, with legal battles, parenting challenges, and family dynamics serving as both obstacles and catalysts.

Symbolism of Holidays and Seasons

The progression from Christmas to Christmas, with key events tied to holidays and seasonal changes, underscores the themes of renewal, tradition, and the possibility of new beginnings. The first snow, Christmas morning, and other festive moments are used to heighten emotional stakes and signal turning points.

Art as Emotional Expression

Hannah's sketchbook serves as a silent diary, revealing her feelings for Caroline before she can articulate them. The act of sharing her art becomes a pivotal moment of vulnerability and trust, transforming the unspoken into the undeniable.

Found Family and Chosen Community

The story challenges traditional notions of family, showing how love, support, and commitment can be found and built outside of blood ties. Caroline, Hannah, and Abbie create a new family unit, supported by friends and community, illustrating the power of chosen bonds.

Foreshadowing and Circular Structure

The novel uses callbacks—such as the coffee cup, holiday parties, and family dinners—to create a sense of continuity and growth. Early misunderstandings and missed opportunities are revisited and resolved, giving the narrative a sense of closure and fulfillment.

Internal and External Conflict

The characters' internal struggles with trust, vulnerability, and self-worth are mirrored by external challenges—Michael's interference, legal battles, and societal expectations. The resolution of these conflicts is both personal and collective, requiring courage, honesty, and mutual support.

Analysis

When You Least Expect It is a masterclass in the slow-burn romance, using the familiar trappings of holiday fiction to explore deeper themes of healing, trust, and the redefinition of family. Haley Cass crafts a narrative that is as much about personal transformation as it is about falling in love, showing how two women—each scarred by disappointment and loss—find in each other the courage to hope again. The novel's strength lies in its nuanced portrayal of trauma and recovery, the authenticity of its characters, and its celebration of chosen family. In a world where cynicism often feels safer than vulnerability, the story argues for the radical possibility of joy, the necessity of risk, and the quiet magic that can be found in everyday acts of care. Ultimately, it is a testament to the idea that love, when it arrives, may not look like what we expect—but it is always worth fighting for.

Last updated: July 15, 2025