Tinder, Tattoos, and Betrayal

Tattoo artist Billie's life is upended when she discovers her boyfriend Kaiden cheating with multiple women via Tinder. Instead of a meltdown, she orchestrates a legendary revenge: inviting all his flings to her shop for a "birthday surprise," then tattoos the Tinder logo on his arm in front of them. The fallout is explosive, leaving Billie single, humiliated, and questioning her trust in men. In the chaos, a stranger—her new landlord, Colby—witnesses the spectacle, setting the stage for an unexpected connection. Billie's pain is raw, but her resilience and wit shine through, even as she swears off dating and love.

The Landlord's Unexpected Entrance

Colby, a single dad and architect, owns the building where Billie's tattoo shop is located. Their first real meeting is a disaster: he walks in on her revenge scene, gets mistaken for a customer, and is promptly insulted. Later, Colby's daughter Saylor becomes enchanted by Billie's art, drawing the two adults together. Despite their differences—Billie's edgy, guarded persona and Colby's responsible, gentle nature—an undeniable spark forms. Both are wary: Billie from heartbreak, Colby from the demands of single parenthood. Yet, their lives begin to intertwine, hinting at possibilities neither expected.

Daddy, Daughter, and Destiny

Colby's devotion to his daughter Saylor is unwavering, filling the void left by her absent mother. Billie, despite her tough exterior, is charmed by Saylor's innocence and creativity. A chance encounter leads to Billie helping Saylor pick out a tattoo design for Colby, deepening the bond between all three. The warmth of their interactions contrasts with Billie's recent pain, and Colby's cautious heart begins to thaw. The trio's chemistry is palpable, and the seeds of a found family are sown, even as both adults resist the pull.

Undateable Attraction Ignites

Billie and Colby's mutual attraction simmers beneath the surface, complicated by Billie's "no dating" rule and Colby's responsibilities. Their flirtation is playful, laced with banter and longing glances. When Colby helps fix Billie's broken AC, the physical closeness and accidental touches ignite their chemistry. Both try to keep things platonic, but the tension is undeniable. They invent "undates"—unromantic hangouts meant to keep things safe. Yet, every undate only draws them closer, blurring the lines between friendship and something more.

Rules, Risks, and Revelations

As undates become more frequent, Billie and Colby open up about their pasts. Billie reveals her history of betrayal and her complicated relationship with her mother. Colby shares the story of Saylor's birth and her mother's abandonment. Vulnerability deepens their connection, but also raises the stakes. Billie's fear of becoming a stepmother and Colby's worry about exposing Saylor to heartbreak keep them cautious. Yet, their emotional intimacy grows, and the risk of falling in love becomes real.

Past Hurts, Present Fears

Billie's friends urge her to give Colby a chance, but her fear of repeating past mistakes holds her back. Colby's friends, meanwhile, tease him about his growing feelings. Both are haunted by previous relationships—Billie by cheaters, Colby by the mother of his child. When jealousy flares (over a tattoo client, a poker night, or a near-threesome), insecurities surface. The couple's attempts to keep things lighthearted are tested by the depth of their feelings and the shadows of their histories.

The Undate Experiment Begins

Billie and Colby's undates become increasingly intimate: IKEA trips, laundry folding, and family dinners. They share laughter, inside jokes, and moments of tenderness. Saylor's affection for Billie grows, and the three form a makeshift family. Yet, the "no dating" rule becomes harder to enforce. Both struggle with the desire to cross the line, knowing that doing so could change everything. The emotional stakes rise as they realize friendship may not be enough.

Lines Blurred, Hearts Stirred

The tension between Billie and Colby finally erupts. A passionate kiss breaks the undate rules, unleashing a flood of pent-up longing. Their physical connection is electric, but it's the emotional vulnerability that truly binds them. Both are terrified—Billie of losing herself, Colby of risking Saylor's heart. Yet, they can't stay away from each other. The boundaries between friends and lovers dissolve, and they surrender to the possibility of real love.

Jealousy, Jokes, and Judgments

As Billie and Colby grow closer, the world around them intrudes. Friends, exes, and even clients weigh in on their relationship. Jealousy rears its head—over harmless flirtations, old flames, and the ever-present specter of Saylor's mother. Billie's insecurities about being a stepmother intensify, while Colby worries about protecting his daughter. Their love is tested by misunderstandings, outside opinions, and the fear of repeating old patterns.

Secrets, Setbacks, and Second Chances

Just as Billie and Colby find happiness, Saylor's biological mother, Maya, reappears—threatening custody and demanding a place in Saylor's life. The couple is thrown into turmoil, forced to navigate legal battles, emotional blackmail, and the possibility of losing Saylor. Maya's manipulations force Colby into a sham marriage, and Billie must step back for Saylor's sake. The pain of separation is acute, but their love endures, tested by the harshest of circumstances.

The Ex Returns, Chaos Erupts

Colby's marriage to Maya is a desperate act to protect his daughter. Billie, heartbroken, supports his decision, even as it means stepping out of his life. Both suffer in silence, longing for each other but prioritizing Saylor's well-being. Letters, longing, and sleepless nights mark their separation. The ordeal exposes the depth of their love and the strength of their character, as they endure for the sake of family.

Custody, Courts, and Compromise

The sham marriage is scrutinized by immigration authorities, leading to invasive interviews and the constant threat of exposure. Colby and Maya must pretend to be a couple, while Billie and Colby remain apart. The stress is immense, and the risk of losing Saylor looms large. Ultimately, Maya's conscience awakens, and she confesses the truth, freeing Colby from the marriage and legal peril. The ordeal leaves scars, but also clears the way for healing.

Sacrifice, Silence, and Separation

During their forced separation, Billie and Colby communicate only through unsent letters and longing glances. Both are tempted by jealousy and doubt, but their love remains steadfast. Friends provide support, but the ache of missing each other is ever-present. The experience deepens their appreciation for what they have, and prepares them for a future built on trust and resilience.

Letters, Longing, and Letting Go

With Maya gone and the legal nightmare over, Billie and Colby reunite. Their love, tested by fire, is stronger than ever. Saylor welcomes Billie back with open arms, and the trio begins to heal. The couple reflects on the lessons learned: the importance of honesty, sacrifice, and choosing each other every day. Their reunion is sweet, passionate, and full of hope for the future.

Truths Unveiled, Trust Rebuilt

Billie and Colby confront the wounds of the past—her fears of abandonment, his guilt over the sham marriage. Through open communication and vulnerability, they rebuild trust. Saylor's acceptance cements their bond as a family. The couple celebrates their love with friends and family, grateful for the second chance they fought so hard to earn.

Rooftop Reunion, Hearts Aligned

Colby surprises Billie with a romantic rooftop dinner, symbolizing a return to hope and joy after hardship. They share laughter, tears, and passionate reconnection under the stars. Saylor's trust is restored, and the family's future feels secure. The city lights bear witness to a love that has survived betrayal, loss, and every obstacle. Together, they look forward to a life built on love, laughter, and the courage to begin again.

Family Forged, Future Promised

With the past behind them, Billie and Colby marry in a joyful celebration surrounded by friends and family. Saylor, now officially calling Billie "Mom," completes their family. The couple's journey—from heartbreak and chaos to healing and hope—serves as a testament to the power of love, forgiveness, and resilience. Their story ends not with perfection, but with the promise to face life's challenges together, forever changed and forever united.

Characters

Billie Holland

Billie is a talented tattoo artist with a sharp wit and a guarded heart. Scarred by betrayal and a difficult relationship with her mother, she uses humor and defiance as armor. Her journey is one of learning to trust again, especially as she falls for Colby and forms a bond with his daughter, Saylor. Billie's struggle with vulnerability, fear of motherhood, and the risk of loving a single dad are central to her arc. Through pain, sacrifice, and self-discovery, she transforms from a woman afraid of love to one who embraces family and commitment.

Colby Lennon

Colby is an architect and single dad whose life revolves around his daughter, Saylor. Abandoned by Saylor's mother, he is cautious, responsible, and deeply loving. Colby's journey is about balancing his own needs with those of his child, learning to open his heart to Billie, and facing the moral dilemmas posed by Maya's return. His integrity, patience, and willingness to sacrifice for those he loves make him a quietly heroic figure. Colby's growth is marked by vulnerability, resilience, and the courage to fight for happiness.

Saylor Lennon

Saylor is Colby's young daughter, whose sweetness and creativity draw Billie and Colby together. Her longing for a mother and her instant affection for Billie are poignant. Saylor's presence forces both adults to confront their fears and desires, serving as the emotional center of the story. Her innocence, trust, and resilience highlight the stakes of every decision, and her eventual acceptance of Billie as "Mom" is the story's emotional climax.

Maya Moreno (Raven)

Maya is Saylor's biological mother, whose abandonment and later return drive the central conflict. Her actions are initially selfish and manipulative, but her backstory—marked by trauma and guilt—adds complexity. Maya's struggle with mental health, shame, and the desire for redemption humanize her, even as she threatens the happiness of the main characters. Her ultimate act of confession and departure is both a release and a bittersweet resolution.

Deek

Deek is Billie's best friend and fellow tattoo artist. Outspoken, protective, and fiercely loyal, he provides both humor and wisdom. Deek challenges Billie to face her fears, supports her through heartbreak, and isn't afraid to call out her self-sabotage. His presence grounds Billie, offering a safe space for honesty and growth.

Holden

Holden is Colby's friend and building co-owner, known for his musical talent and wild ways. Beneath his carefree exterior lies a deep loyalty and surprising insight. Holden's own romantic struggles mirror and contrast with Colby's, and his support is instrumental during crises. He provides levity, encouragement, and, at times, the push Colby needs to pursue happiness.

Owen

Owen, another building co-owner, is the practical, work-focused friend. He offers stability and a grounded perspective, often mediating conflicts and providing a reality check. Owen's own search for meaning and connection adds depth to the friend group, and his unwavering support is a quiet but essential force.

Brayden

Brayden rounds out the quartet of friends, serving as a mediator and source of comic relief. His easygoing nature and quick wit help diffuse tension, and his loyalty to Colby is unwavering. Brayden's presence reinforces the theme of chosen family and the importance of friendship in weathering life's storms.

Justine

Justine is Billie's receptionist and friend, offering warmth, encouragement, and a steadying influence. She helps manage the chaos of the tattoo shop and provides a sounding board for Billie's doubts and dreams. Justine's quiet strength and kindness are a subtle but vital part of Billie's support system.

Saylor's Nanny (Kay)

Kay is Saylor's nanny, providing stability and routine in Colby's busy life. Though a minor character, her reliability and affection for Saylor allow Colby the freedom to pursue love and work, and her presence underscores the theme of community and shared responsibility.

Plot Devices

Alternating Perspectives

The story alternates between Billie and Colby's points of view, allowing readers intimate access to their thoughts, fears, and desires. This structure heightens tension, reveals misunderstandings, and builds empathy for both characters. The dual perspective is crucial in exploring themes of trust, vulnerability, and the complexity of blended families.

"Undates" as a Narrative Device

The concept of "undates"—deliberately unromantic hangouts—serves as both a comedic device and a metaphor for the characters' fear of intimacy. Each undate brings Billie and Colby closer, exposing the futility of trying to control or deny genuine connection. The gradual erosion of these rules mirrors their journey toward trust and love.

Foreshadowing and Symbolism

Tattoos are more than body art—they symbolize identity, pain, and transformation. The recurring motif of keys and locks represents vulnerability and the search for belonging. Early scenes foreshadow later conflicts: Billie's revenge tattoo hints at her capacity for both pain and healing, while Saylor's longing for a mother prefigures the family's eventual union.

The Return of the Ex

Maya's reappearance is a classic plot twist, forcing the protagonists to confront their deepest fears and make painful sacrifices. The custody battle and sham marriage raise the stakes, testing the couple's commitment and resilience. This device drives the narrative toward its emotional climax and ultimate resolution.

Letters and Unsent Communication

During their separation, Billie and Colby write unsent letters, expressing feelings they cannot share aloud. These letters serve as a window into their souls, deepening the reader's understanding of their love and pain. The eventual sharing of these letters is a turning point, facilitating forgiveness and reunion.

Found Family and Community

Friends, colleagues, and chosen family play pivotal roles, offering support, advice, and comic relief. Their presence underscores the idea that love and belonging are built, not given, and that healing often requires a village.

Analysis

The Rules of Dating is a contemporary romance that subverts the genre's clichés by embracing the messiness of real life: betrayal, single parenthood, trauma, and the complexities of blended families. At its core, the novel is about the courage to love again after heartbreak, the sacrifices required to build trust, and the transformative power of vulnerability. Billie and Colby's journey is marked by humor, pain, and growth, reflecting the reality that love is rarely simple or easy. The story challenges traditional notions of family, highlighting the importance of chosen bonds and the healing that comes from community. Through alternating perspectives, rich symbolism, and a cast of memorable supporting characters, the novel explores themes of forgiveness, resilience, and the willingness to fight for happiness. Ultimately, The Rules of Dating is a celebration of imperfect people finding their way to each other, proving that true love is not about following rules, but about breaking them together.

Last updated: October 20, 2025