Small Town, Big Dreams

Ramona, a thirty-one-year-old waitress and costume designer in the small town of Clover Lake, New Hampshire, has spent her adult life caring for her younger sister, Olive, after their mother's abandonment and their father's accident. Her dreams of a career in costume design have been on hold for over a decade, replaced by routine and responsibility. As Olive prepares to leave for college, Ramona faces the daunting prospect of an empty nest and wonders if it's too late to chase her own ambitions. Her best friend April pushes her to take risks, but Ramona is hesitant, clinging to the comfort of her small-town world even as she feels the ache of deferred dreams.

Hollywood Descends on Clover Lake

The town buzzes with excitement as a major Hollywood production arrives to film a queer romantic comedy, bringing celebrities, industry legends, and a whirlwind of change. For Ramona, the most thrilling news is that her idol, Oscar-winning costume designer Noelle Yang, will be leading the film's wardrobe department. The arrival of the film crew disrupts the town's rhythms, but it also presents Ramona with a once-in-a-lifetime chance to connect with her dreams. Meanwhile, the town's residents—curious, nosy, and sometimes small-minded—react to the influx of outsiders with a mix of awe and suspicion, setting the stage for a summer of transformation.

First Kiss, Forgotten Names

Eighteen years earlier, a thirteen-year-old Ramona met a mysterious girl, "Lolli," on the lakeshore during a difficult summer. They shared laughter, secrets, and a first kiss, never exchanging real names. That night became a cherished, private memory for Ramona—a symbol of hope and possibility amid loss. Unbeknownst to her, "Lolli" was Dylan Monroe, now a famous actress and the star of the film shooting in Clover Lake. When Dylan arrives in town, neither recognizes the other at first, but the emotional resonance of their shared past lingers beneath the surface, waiting to be rediscovered.

Stardom's Shadow and Scandal

Dylan, the daughter of rock legends, is infamous for her wild behavior and tabloid scandals. She's eager to reinvent herself by taking on her first romantic lead in a queer rom-com, but Hollywood's skepticism and her own insecurities threaten to undermine her. Dylan's recent breakup with another celebrity, Jocelyn, has left her raw and defensive, and her every move is scrutinized by the press. As she tries to prepare for her role as a small-town waitress, she's forced to confront her own loneliness, her fraught relationship with her parents, and the challenge of being seen as more than a headline.

Reunion at the Diner

When Dylan is sent to Clover Moon Café for "waitress training," Ramona is assigned to show her the ropes. The two women feel an inexplicable connection, a sense of déjà vu that neither can place. Their interactions are awkward, charged, and unexpectedly intimate, as Ramona's steady competence and Dylan's vulnerability draw them together. The town watches with fascination as the celebrity and the local girl navigate their growing attraction, unaware of the history that binds them. Meanwhile, Ramona's best friend April and her sister Olive encourage her to seize the opportunity, both for her career and her heart.

Old Wounds, New Hopes

Ramona's life has been defined by loss—her mother's abandonment, her father's injury, and the responsibility of raising Olive. These wounds make her cautious, but also fiercely loyal and nurturing. Dylan, too, is haunted by her parents' chaotic love and neglect, and by the pressure of living in their shadow. As the two women spend more time together, they begin to share their stories, finding solace and understanding in each other's pain. Their connection deepens, but both are afraid to hope for more, wary of repeating old patterns of disappointment.

Training Days and Tangled Hearts

As Dylan learns the ins and outs of diner life, she and Ramona grow closer, sharing laughter, frustrations, and moments of unexpected intimacy. Their chemistry is undeniable, but both are hesitant to act on it—Ramona out of fear of being hurt or used, Dylan out of fear of not being enough. The town's gossip mill churns, and the film crew's presence only heightens the scrutiny. Meanwhile, Ramona's dreams of working in costume design are rekindled by her proximity to Noelle Yang, and Dylan finds herself longing for a sense of normalcy and belonging she's never known.

Costume Dreams Rekindled

Encouraged by April and Olive, Ramona begins to believe that her dreams aren't as out of reach as she once thought. She starts to take small steps—showing her portfolio, volunteering to help with costumes, and eventually catching Noelle Yang's attention. Noelle recognizes Ramona's talent and offers her a chance to assist on set, a pivotal moment that forces Ramona to confront her fears and insecurities. The possibility of a new life, one where she can be both artist and caretaker, begins to take shape, even as her feelings for Dylan grow more complicated.

The Past Comes Calling

As Ramona and Dylan spend more time together, fragments of their shared past begin to surface. A chance conversation, a song, or a familiar gesture triggers memories of that long-ago night by the lake. When the truth finally emerges—that they were each other's first kiss—the revelation is both joyful and bittersweet. It deepens their bond, but also brings unresolved emotions to the fore. Both women must decide whether to let the past define them or to use it as a foundation for something new.

Fake Dating, Real Feelings

Under pressure from her publicist and the film's producers, Dylan agrees to a fake dating arrangement with Ramona to improve her image. What begins as a strategic move quickly becomes emotionally fraught, as real feelings develop on both sides. Ramona, unaware of the arrangement's origins, is swept up in the romance, while Dylan struggles with guilt and the fear of being unworthy of genuine love. The line between performance and authenticity blurs, and secrets threaten to unravel the fragile trust they've built.

Secrets, Lies, and Longing

The truth about the fake dating arrangement and Ramona's ambitions in costume design come to a head, shattering the trust between them. Both feel betrayed—Dylan by the fear that she's been used, Ramona by the realization that she was part of a publicity stunt. Their breakup is public and painful, amplified by the ever-present gaze of the town and the media. Each retreats into her own world, nursing wounds old and new, and questioning whether love is worth the risk of heartbreak.

The Breakup Scene

As the film's climactic breakup scene is filmed, the parallels between fiction and reality are impossible to ignore. Dylan channels her pain into her performance, delivering a raw and moving portrayal that earns her the respect of her peers and the director. Ramona, meanwhile, throws herself into her work with Noelle, earning a job offer that could change her life. Both women are forced to confront what they truly want—and what they're willing to risk to get it.

Family Ties and Forgiveness

In the aftermath of the breakup, both Ramona and Dylan turn to their families for support and understanding. Ramona helps Olive reconnect with their estranged mother, facing her own unresolved feelings in the process. Dylan returns to LA and finally has an honest conversation with her parents, breaking the cycle of avoidance and blame that has defined their relationship. Through these acts of vulnerability and forgiveness, both women begin to heal, making space for new possibilities.

Dreams Deferred, Dreams Awakened

Offered a permanent position with Noelle Yang in LA, Ramona must decide whether to leave Clover Lake and the life she's always known. With her family's encouragement, she chooses to pursue her dreams, moving to LA and building a new life as a costume designer. The transition is bittersweet, marked by homesickness and self-doubt, but also by a growing sense of agency and fulfillment. For the first time, Ramona allows herself to want more—and to believe she deserves it.

Grand Gestures Under the Stars

Dylan, realizing that she cannot let fear dictate her life, makes a grand romantic gesture. She posts nightly photos from the Griffith Observatory, a place she once told Ramona she'd wait for her, using secret symbols from their shared past. Ramona, with April and Olive's encouragement, recognizes the message and rushes to meet Dylan under the stars. Their reunion is emotional and cathartic, as both women apologize, forgive, and confess their love, choosing each other despite the risks.

Second Chances, True Love

Reunited in LA, Ramona and Dylan commit to building a life together, one that honors both their dreams and their vulnerabilities. They navigate the challenges of fame, family, and ambition, learning to communicate honestly and support each other's growth. Their love is imperfect but resilient, rooted in shared history and a willingness to try again. As they settle into their new home, they find joy in the ordinary and the extraordinary, proving that it's never too late to dream—or to love.

Homecoming and New Beginnings

Nearly a year later, Ramona and Dylan return to Clover Lake for a summer visit, surrounded by family and friends. The town that once felt confining now feels like a place of belonging and celebration. Olive and Marley are together, April is finding her own path, and Ramona's career is flourishing. As they dance on the pier to the song that first brought them together, Ramona and Dylan reflect on how far they've come—and how much more they have to dream, together.

Characters

Ramona Riley

Ramona is a thirty-one-year-old waitress and costume designer whose life has been shaped by loss and responsibility. After her mother's abandonment and her father's accident, she put her dreams on hold to raise her younger sister, Olive. Ramona is nurturing, loyal, and self-sacrificing, but also struggles with feelings of invisibility and fear of taking risks. Her journey is one of reclaiming her own desires—both romantic and professional—and learning that she is worthy of love and ambition. Through her relationship with Dylan and her eventual leap into the world of costume design, Ramona transforms from a woman defined by duty to one who chooses herself, embracing vulnerability and hope.

Dylan Monroe

Dylan is a Hollywood actress known for her wild reputation and tabloid scandals, the daughter of rock legends Jack Monroe and Carrie Page. Beneath her bravado and fame lies a deep loneliness and a longing to be seen for who she truly is. Haunted by a chaotic childhood and a string of failed relationships, Dylan is both magnetic and self-destructive, craving connection but terrified of being hurt or used. Her journey with Ramona forces her to confront her own patterns, seek forgiveness, and risk vulnerability. Dylan's arc is one of self-acceptance, learning to trust, and choosing love not as a performance, but as a real, messy, and beautiful act.

April Evans

April is Ramona's lifelong best friend, a tattoo artist with a sharp wit and a passionate heart. She pushes Ramona to pursue her dreams and refuses to let her settle for less than she deserves. April's own struggles with love and loss—particularly her failed engagement—mirror Ramona's fears, but she channels her pain into loyalty and encouragement. April is the voice of tough love, comic relief, and unwavering support, embodying the power of chosen family and the importance of having someone who believes in you, even when you don't believe in yourself.

Olive Riley

Olive is Ramona's much-younger sister, raised by Ramona after their mother left. Smart, independent, and ready to leave for college, Olive represents both the sacrifices Ramona has made and the possibilities that await. Her own journey—navigating identity, love, and family—parallels Ramona's, and her eventual reconciliation with their mother provides a poignant counterpoint to Ramona's healing. Olive's growth and happiness are both a source of pride and a catalyst for Ramona to finally choose herself.

Noelle Yang

Noelle is an Oscar-winning costume designer and Ramona's idol. She is sharp, demanding, and brilliant, recognizing Ramona's talent and offering her the chance to break into the industry. Noelle serves as both a symbol of what's possible and a test of Ramona's courage. Her mentorship is transformative, pushing Ramona to claim her place in a world she once thought was closed to her. Noelle's presence also forces Ramona to confront her own fears of inadequacy and to step into her power as an artist.

Jack Monroe and Carrie Page

Dylan's parents are legendary musicians whose tumultuous relationship and neglectful parenting have left deep scars. Their journey toward sobriety, reconciliation, and honest communication with Dylan is a crucial part of the novel's exploration of family, forgiveness, and the possibility of change. Jack and Carrie are both larger-than-life and deeply human, embodying the complexities of love, regret, and the hope for second chances.

Blair Emmanuel

Blair is Dylan's former co-star and on-screen nemesis, brought in as her romantic lead after a casting shakeup. Their history is fraught with competition and resentment, but through the course of filming, they find common ground and mutual respect. Blair's presence challenges Dylan to confront her own insecurities and to grow as both an actor and a person. Their evolving relationship underscores the novel's themes of growth, forgiveness, and the power of honest connection.

Jocelyn Gareth

Jocelyn is Dylan's recent ex, a fellow celebrity whose betrayal and ambition have left Dylan wounded and wary. Jocelyn's actions—pursuing a record deal with Dylan's father behind her back—mirror Dylan's deepest fears of being used and discarded. Her presence in the story forces Dylan to reckon with her own patterns and to choose a different path with Ramona, one rooted in honesty and trust.

Leigh Reynolds

Leigh is a nonbinary, lesbian friend of Ramona and April, known for their charm, wit, and casual approach to relationships. Leigh provides both levity and perspective, reminding the main characters not to take themselves too seriously and offering a counterpoint to the intensity of Ramona and Dylan's romance. Their presence highlights the diversity and vibrancy of queer community and friendship.

Penny Hampton

Penny is the author of the town's unofficial blog, Penny for Your Thoughts, and serves as both a source of comic relief and a narrative device for tracking the town's reactions to the unfolding drama. Her posts reflect the ways in which small communities both support and scrutinize their own, and her observations provide a chorus of commentary on love, ambition, and the courage to change.

Plot Devices

Dual Timelines and Memory

The novel uses flashbacks and dual timelines to reveal the formative night Ramona and Dylan shared as teenagers, gradually connecting it to their present-day relationship. This device deepens the emotional stakes, showing how early wounds and moments of hope can echo through a lifetime. The slow unveiling of their shared history adds layers of poignancy and inevitability to their romance, making their reunion feel both fated and hard-won.

Small Town vs. Hollywood

The juxtaposition of Clover Lake's insular, routine-driven life with the chaos and glamour of Hollywood serves as both backdrop and metaphor. The arrival of the film crew disrupts the town's equilibrium, forcing characters to confront their own limitations and desires. The tension between staying and leaving, safety and risk, is embodied in Ramona's journey from waitress to costume designer, and in Dylan's struggle to be seen as more than a celebrity.

Fake Dating and Publicity

The fake dating arrangement between Dylan and Ramona, orchestrated for publicity, becomes a crucible for exploring authenticity, vulnerability, and the dangers of self-protection. As real feelings develop, the line between performance and truth blurs, forcing both women to confront their own fears of being used or abandoned. The device also allows for commentary on the pressures of fame, the commodification of queer love, and the courage required to be honest in a world that rewards artifice.

Parallel Character Arcs

Both Ramona and Dylan are shaped by abandonment, loss, and the weight of family expectations. Their parallel arcs—learning to forgive, to choose themselves, and to risk love—are woven together through shared experiences and mutual support. The novel uses their mirrored struggles to explore broader themes of resilience, the possibility of change, and the transformative power of love.

Grand Gesture and Symbolism

The use of the Griffith Observatory and the cherry/lollipop emojis as a secret signal is a classic grand gesture, tying together the novel's themes of fate, memory, and the willingness to try again. This device provides a cathartic, emotionally satisfying resolution, affirming that love is both a choice and a leap of faith.

Analysis

Dream On, Ramona Riley is a heartfelt, emotionally rich novel that explores what it means to choose yourself after years of self-sacrifice and fear. Through the intertwined journeys of Ramona and Dylan, the story examines the long shadows cast by family wounds, the seductive safety of routine, and the terrifying exhilaration of chasing your dreams. The novel is unflinching in its portrayal of queer love—not as a sanitized, idealized fantasy, but as a messy, vulnerable, and deeply human experience. It interrogates the ways in which we perform for others, the dangers of hiding behind old stories, and the necessity of honesty—with ourselves and with those we love. Ultimately, the book is a celebration of second chances, the power of community, and the belief that it's never too late to become the person you were meant to be. Its message is clear: love is worth the risk, and dreams deferred can still come true if you dare to reach for them.

Last updated: March 17, 2026