The Rom Con by Devon Daniels Summary, Characters and Themes
The Rom Con by Devon Daniels is a smart, witty romantic comedy that cleverly critiques modern dating culture while embracing the heart of classic romance. At the center is Cassidy Sutton, a sharp-minded feminist journalist who sets out to expose the misogyny of traditional gender roles by ironically adopting them.
Her target?
Jack Bradford, the co-founder of a media company she sees as everything wrong with male-driven media.
What begins as an undercover professional mission quickly spirals into a deeply personal journey. Devon Daniels crafts a story that balances humor, social commentary, and emotional growth, offering readers both entertainment and reflection.
Summary
Cassidy Sutton is a bold and driven editor living in New York City. After a disappointing breakup, she vents her frustration about the state of modern dating to her grandmother during her 90th birthday celebration.
Her grandmother jokingly hands her an old 1950s dating article titled “125 Tips to Hook a Husband.” What starts as a joke quickly turns into a challenge—and then a professional opportunity.
Cassidy pitches the idea of following the retro advice as a social experiment to her boss at Siren, a feminist publication. The pitch is accepted with enthusiasm—especially if Cassidy agrees to be the one conducting the experiment.
Thus, “Operation Rom Con” is born: Cassidy will follow the outdated dating tips and write an exposé on how absurd they are in today’s world.
Cassidy stages her first “meet-cute” at a press event by faking a clumsy fall and spilling her purse. There, she meets Jack Bradford, a confident and mysterious man who quickly sees through her act.
She later learns that Jack is the co-founder of Brawler, a media outlet known for content that starkly contrasts with Siren’s values. Recognizing the potential for a juicy story, Cassidy decides to use Jack as her primary subject for the experiment.
Their first outing is a high-profile event at the US Open, where Cassidy adopts a demure and supportive persona. She plays up the traditional traits recommended in the vintage guide—dressing modestly, being agreeable, and flattering Jack’s masculinity.
Despite her skepticism, she finds herself charmed by his wit and depth. Jack, too, appears genuinely intrigued by her.
Cassidy continues the act over several dates, using the guide’s more ridiculous tips, such as pretending helplessness and baking cookies. To her surprise, Jack responds more to the moments when her real personality slips through.
As the experiment progresses, Cassidy’s internal conflict deepens. She finds herself genuinely enjoying Jack’s company and questioning her initial assumptions about him.
While she hoped to expose his sexism, she discovers that the worst of Brawler’s content stems from Jack’s partner, not Jack himself. Meanwhile, at Siren, her editor pushes for a dramatic, career-defining story, while her roommate Natalia warns her about the emotional toll of deception.
Cassidy and Jack grow closer, and their physical chemistry becomes undeniable. During a sailing trip and other outings, Jack continues to surprise Cassidy with his thoughtfulness and vulnerability.
She starts to pull back from the act, letting her true self emerge. But the secret of her article looms large.
Her editor pressures her to submit the piece, and Cassidy writes a draft that reflects her conflicted feelings but doesn’t send it immediately. Things fall apart when Jack discovers a version of the article through a mutual contact.
Feeling betrayed, he confronts Cassidy and ends their relationship. The article is eventually published and goes viral, but the reception is mixed.
Cassidy faces backlash for her ethics and feels isolated at work. Her grandmother’s wisdom helps her see that real love requires honesty and courage.
Determined to make amends, Cassidy writes a follow-up piece taking full responsibility and publicly apologizes to Jack. This time, the article is authentic, vulnerable, and humble.
Jack reads it and reaches out. In a quiet, heartfelt reconciliation, they agree to move forward honestly, without facades or schemes.
They decide to start fresh, this time not as subjects of an article or adversaries in a media war, but as two people who see and respect each other for who they really are.
The Rom Con ends not with dramatic declarations, but with a grounded and hopeful reunion—reminding readers that love, like good journalism, must be based on truth.
Characters
Cassidy Sutton
Cassidy is the vibrant, sharp-witted protagonist whose journey forms the emotional and thematic backbone of The Rom Con. As an ambitious editor at Siren, a feminist media outlet, Cassidy initially approaches life—and particularly dating—with a blend of cynicism and sarcasm.
After a disappointing breakup, she channels her frustrations into an undercover project that aims to expose misogyny by ironically adopting outdated 1950s dating tips. Her decision to use this retro advice as the framework for a journalistic stunt reveals her desire to assert agency while navigating a personal world that has left her disillusioned.
Yet, Cassidy is far from a one-dimensional career woman trope. Over the course of the narrative, she is transformed by her emotional entanglement with Jack Bradford.
As she attempts to caricature herself into a “perfect” submissive woman to bait Jack, she begins to unravel her own layers of performance. This happens not just for the sake of the article but in how she understands intimacy, honesty, and identity.
Her growing inner conflict, especially when confronted with Jack’s actual character, forces her to reconsider her values. Cassidy’s arc is ultimately one of integrity and emotional growth.
She shifts from being guarded and strategic to open and vulnerable. Cassidy becomes someone willing to risk her public image for the sake of personal truth and reconciliation.
In doing so, she evolves into a more grounded and self-aware version of herself.
Jack Bradford
Jack Bradford begins as a potentially problematic romantic lead, embodying everything Cassidy’s publication, Siren, is meant to critique. Co-founder of Brawler, a male-dominated media platform often positioned in opposition to Siren’s values, Jack is introduced as a symbol of the enemy.
However, it quickly becomes clear that Jack defies simple categorization. Beneath his confident, charismatic demeanor is a thoughtful, introspective man who has been unfairly judged by association with Brawler’s more aggressive co-founder, Tom.
Jack’s interactions with Cassidy, even before he knows of her deception, are marked by an openness to challenge and a capacity for nuanced conversation. He is never a simplistic foil for Cassidy’s ideology.
Instead, he complicates her worldview. Jack’s ability to see through performative behavior and his appreciation for authenticity make him a compelling and worthy counterpart.
His eventual discovery of Cassidy’s article and the emotional fallout that ensues reveal his vulnerability, but also his maturity. His willingness to forgive, while not condoning the deception, underscores his emotional intelligence.
Jack’s character arc moves from being a misunderstood media figure to a man who values truth and connection over public image.
Natalia
Natalia serves as Cassidy’s confidante and emotional anchor throughout the story. She is supportive without being sycophantic, providing the grounding presence Cassidy needs as she navigates both her professional ruse and her growing feelings for Jack.
Natalia acts as a moral sounding board—encouraging Cassidy when she’s uncertain but also challenging her when her motivations become murky. While not a central figure in terms of plot action, Natalia’s role is indispensable as a catalyst for Cassidy’s self-reflection.
She represents the voice of reason. Natalia reminds Cassidy of the ethical lines she risks crossing and helps her confront the emotional weight of her actions.
She embodies the quiet wisdom and loyalty of true friendship.
Themes
Authenticity vs. Performance
A central theme in The Rom Con is the tension between authenticity and performance in relationships, especially modern dating. Cassidy Sutton embarks on a deceptive experiment to apply outdated 1950s dating advice as a joke-turned-investigative piece.
Initially, her actions are purely performative—she bakes cookies she doesn’t eat, compliments masculinity she doesn’t genuinely admire, and stages meet-cutes to ensnare her target. As she spends more time with Jack, she begins to realize that these performances aren’t just about fooling someone else—they’re also compromising her own identity.
The deeper Cassidy goes into the act, the more fractured her sense of self becomes, until she finds herself conflicted about who she really is. Jack, meanwhile, becomes a mirror for Cassidy’s internal struggle.
He appears to be everything she stands against but turns out to be surprisingly genuine. The irony becomes clear: while Cassidy performs to unmask Jack, it is Jack’s consistent authenticity that unravels her performance.
Her eventual confession and public retraction mark the moment she chooses honesty over ambition. Through this theme, the novel questions whether connection can ever flourish in the absence of sincerity and highlights the emotional cost of hiding behind social scripts—whether vintage or modern.
Modern Feminism and Its Contradictions
Cassidy’s career at Siren, a feminist media outlet, sets the stage for a nuanced exploration of feminism and its contemporary contradictions. She is a firm believer in gender equality, outspoken about toxic masculinity, and suspicious of traditional gender roles.
Yet she finds herself embroiled in a project that asks her to embody every stereotype feminism seeks to dismantle. This ironic twist exposes the fragility and flexibility of ideology when it’s tested in real-world situations.
Cassidy must confront the possibility that her rigid view of Jack as the co-founder of a “problematic” platform like Brawler might be oversimplified. As Cassidy tries to manipulate him using gender norms, she inadvertently demonstrates how easily those norms can still shape behavior—even when one believes they’ve outgrown them.
The novel doesn’t mock feminism; instead, it presents a thoughtful critique of how ideological purity can falter in the face of human complexity. Cassidy’s evolution from using feminism as a sword to wield against men to a lens for self-awareness and empathy is central to the book’s message.
The theme underscores the idea that true feminism doesn’t lie in blanket condemnation or perfection, but in nuance, growth, and the willingness to acknowledge one’s own biases and mistakes.
Media Ethics and Professional Integrity
The novel raises probing questions about media ethics, particularly the lengths to which journalists might go to generate a compelling story. Cassidy’s undercover operation—disguising herself and manipulating a subject for the sake of content—highlights the ethical gray zones within the world of click-driven journalism.
Initially, her actions are sanctioned by her editor and driven by a desire to critique misogyny. However, as the experiment continues, Cassidy becomes aware of how her journalistic mission is becoming personal and exploitative.
The moment Jack discovers her betrayal not through a public scandal but via a leaked draft speaks volumes about the vulnerability that comes with being misrepresented, even when intentions are noble. The fallout not only damages Cassidy’s relationship with Jack but also tarnishes her reputation, both within Siren and in the public eye.
The viral success of her article does not bring the satisfaction she expects—it instead breeds discomfort, criticism, and alienation. Cassidy’s eventual decision to retract her framing and issue a sincere public apology reflects a restored sense of ethical clarity.
Through this theme, the novel explores how media sensationalism can distort truth, how personal motives can cloud professional judgment, and how redemption is possible only through accountability and transparency.
Love as a Process of Mutual Growth
Rather than framing love as a passive discovery or romantic inevitability, The Rom Con presents it as a process of mutual growth and compromise. Cassidy and Jack begin as ideological adversaries and social experiments—Cassidy intending to expose Jack, Jack treating their dates as casual encounters.
But as their interactions accumulate, so do the layers of understanding between them. Cassidy starts to see Jack not as a symbol of male privilege but as a person with values, vulnerabilities, and wounds.
Jack, for his part, engages seriously with Cassidy, challenging her assumptions without dismissing her outright. Their emotional progression is not marked by grand romantic gestures but by difficult conversations, moments of doubt, and eventually, a shared commitment to honesty.
When their relationship is broken by Cassidy’s betrayal, their eventual reconciliation is not easy or formulaic—it is earned through reflection, apology, and the willingness to rebuild trust. Love, the book suggests, is not just about chemistry or compatibility but about evolving with another person.
Forgiving them, and meeting them where they are. This theme offers a mature, hopeful take on romance, emphasizing that real relationships demand emotional labor and courage from both people.