Collision of Rivals

Annalise O'Neil and Bennett Fox, both creative directors at rival ad agencies, are thrown together when their companies merge. Their first encounter is a comedic disaster involving a parking ticket, a broken windshield wiper, and a tangle of Annalise's hair. The merger means only one of them will keep their job in San Francisco; the other will be transferred to Texas. Their initial animosity is fueled by misunderstandings, competitive banter, and a mutual attraction neither wants to admit. The stage is set for a high-stakes, emotionally charged rivalry where professional ambition and personal chemistry collide.

Office Wars Begin

The merger's terms are revealed: Annalise and Bennett must compete for three major client pitches, with the winner staying in San Francisco and the loser relocating. Their boss, Jonas, tries to keep the peace, but the tension is palpable. Both are determined to win, using every tool at their disposal—Bennett's charm and creative flair, Annalise's meticulous organization and client relationships. Their teams are on edge, and the office becomes a battleground of wit, sabotage, and one-upmanship. Underneath the rivalry, sparks of attraction begin to flicker, complicating their professional lives.

Parking Tickets and Pranks

The parking ticket incident becomes a running joke and a symbol of their escalating prank war. Annalise's attempt to avoid a fine by switching tickets leads to Bennett's car being damaged, and he retaliates by assigning her a "janitor's closet" as her new office. Their interactions are laced with sarcasm, flirtation, and underlying respect. Each prank is a test of boundaries, revealing more about their personalities and vulnerabilities. The office staff watches in amusement and horror as the two creative directors push each other's buttons, setting the tone for their evolving relationship.

Unlikely Alliances

Despite their rivalry, Annalise and Bennett are forced to work together on certain accounts. Their creative approaches clash, but they begin to appreciate each other's strengths. Late nights in the office, brainstorming sessions, and shared frustrations lead to moments of genuine connection. They bond over pizza, vodka shots, and confessions about their personal lives. Annalise's recent breakup and Bennett's guarded heart come to the surface. The line between professional and personal blurs as their mutual respect grows, and the possibility of something more than rivalry emerges.

Family Ties Revealed

Annalise's family owns a winery, one of the key accounts up for grabs. Bennett's attempt to win over her family backfires when he realizes he's been invited to dinner as a potential suitor, not just a business partner. Annalise's mother is a matchmaker, and her stepfather is warm and welcoming. The dinner exposes Bennett's softer side and Annalise's deep loyalty to her family. Their banter takes on a more intimate tone, and both begin to see each other as more than just competitors. The stakes of the competition become personal, and the emotional risks increase.

Ghosts of the Past

Bennett's past is haunted by guilt over a tragic accident involving his best friend, Sophie, and his godson, Lucas. Annalise struggles with the aftermath of her long-term relationship's end and her fear of vulnerability. Both are shaped by loss and regret, which influence their reluctance to trust and love again. As they open up to each other, they find solace in shared pain and understanding. Their emotional walls begin to crumble, and the possibility of healing through connection becomes real. The past looms large, threatening to derail their growing bond.

Lines Crossed

The competition heats up as the client pitches approach. Annalise and Bennett's flirtation turns physical, leading to a passionate night together. Their secret affair is fraught with risk—if discovered, it could cost them both their jobs. The thrill of secrecy intensifies their connection, but also breeds insecurity and jealousy. Office gossip swirls, and their ability to separate work from personal life is tested. The stakes are higher than ever, and both must decide what they're willing to risk for love and career.

Vulnerability and Truth

After a series of misunderstandings and emotional confrontations, Annalise and Bennett are forced to confront their true feelings. Annalise admits her fear of being hurt again, while Bennett reveals the depth of his guilt and self-doubt. Their vulnerability brings them closer, but also exposes the fragility of their relationship. They must choose whether to trust each other and take a leap of faith, or retreat into old patterns of self-protection. The outcome of the competition looms, adding pressure to their already complicated dynamic.

The Jealousy Game

Bennett's jealousy flares when Annalise's ex, Andrew, reappears, and she is forced to work with him on a key account. Miscommunication and suspicion lead to a painful rift. Annalise feels betrayed by Bennett's lack of trust, while Bennett is tormented by his fear of losing her. Their relationship teeters on the edge as professional rivalry and personal insecurity collide. Both must confront their deepest fears and decide if love is worth fighting for, even when it means risking everything.

Breaking Down Walls

After a dramatic confrontation, Annalise and Bennett begin to rebuild trust. They apologize for their mistakes and acknowledge the pain they've caused each other. Bennett opens up about his past, and Annalise offers compassion and support. Their relationship deepens as they learn to communicate honestly and accept each other's flaws. The competition for the job reaches its climax, but both realize that their connection is more important than winning. They make a pact to face whatever comes next together, united by love and mutual respect.

Temptation and Restraint

As the final client pitch approaches, Annalise and Bennett struggle to balance their passion with their professional obligations. Temptation is ever-present, but they exercise restraint to avoid jeopardizing their futures. Their chemistry is undeniable, but they are determined to win (or lose) on their own merits. The tension between them is electric, and every touch, glance, and word is charged with meaning. The outcome of the competition will determine not only their careers, but the future of their relationship.

The Turning Point

A sudden accident puts Annalise's life in danger, forcing Bennett to confront his true feelings. In the hospital, he confesses his love and admits his fear of losing her. The near-tragedy brings clarity to both, and they realize that love is more important than any job or rivalry. Bennett makes a life-changing decision, resigning from the company to stay by Annalise's side. Their relationship is tested, but ultimately strengthened by adversity. They emerge from the crisis with a renewed sense of purpose and commitment.

Confessions and Consequences

As Annalise recovers, she and Bennett face the consequences of their choices. They come clean to their colleagues and families, risking professional fallout for the sake of honesty. Their love is met with skepticism and support in equal measure. Bennett's relationship with his godson, Lucas, is tested as he finally confronts the past and seeks forgiveness. Annalise must decide whether to stay in San Francisco or start anew elsewhere. Together, they navigate the challenges of blending their personal and professional lives, determined to build a future on a foundation of truth.

The Fallout

The aftermath of the competition and the accident forces Annalise and Bennett to reevaluate their priorities. They let go of old grudges, forgive themselves and each other, and make peace with their histories. Bennett's guilt over Sophie's death is eased by Annalise's compassion, and Annalise finds closure with Andrew. They support each other through difficult conversations and painful memories, emerging stronger and more united. The future is uncertain, but they face it together, ready to embrace whatever comes next.

Second Chances

With the competition behind them, Annalise and Bennett start fresh. They launch their own agency, combining their talents and visions. Their relationship flourishes as they learn to work as true partners, both in business and in life. Lucas becomes a central part of their family, and the trio builds a home filled with love, laughter, and second chances. The lessons of the past inform their choices, and they are determined not to repeat old mistakes. Together, they create a life that is richer and more meaningful than either could have imagined alone.

Facing the Past

Bennett and Annalise confront the lingering pain of their pasts, seeking closure and forgiveness. Bennett reconciles with Lucas and finds a way to honor Sophie's memory. Annalise makes peace with her family and her own fears of abandonment. Their journey is marked by honesty, vulnerability, and a willingness to face difficult truths. Through therapy, open communication, and mutual support, they heal together. The scars remain, but they no longer define them. Love becomes the force that transforms pain into growth.

The Final Pitch

The last client pitch is a triumph, not just professionally but personally. Annalise and Bennett prove that they are stronger together than apart. Their agency wins the account, and their reputation as a dynamic duo is cemented. The victory is sweet, but it is their partnership—built on trust, respect, and love—that matters most. They celebrate with friends and family, grateful for the journey that brought them to this moment. The future is bright, and they look forward to building a legacy together.

Love Wins Out

Annalise and Bennett's story concludes with a proposal, a new home, and the promise of a lifetime together. They have overcome rivalry, heartbreak, and personal demons to find true happiness. Their love is imperfect but real, forged in the fires of competition and adversity. Surrounded by family, friends, and the memories of those they have lost, they embrace the future with hope and joy. The final lesson is clear: love is worth fighting for, and sometimes, the person you shouldn't fall for is exactly the one you need.

Characters

Annalise O'Neil

Annalise is a talented creative director whose life is upended by a corporate merger that pits her against Bennett for a single coveted position. She is fiercely organized, loyal to her family, and haunted by the recent end of a long-term relationship. Annalise's competitive spirit masks deep insecurities and a fear of abandonment. Her journey is one of learning to trust again, embracing vulnerability, and finding the courage to love after heartbreak. Through her rivalry and eventual romance with Bennett, she discovers her own strength and the value of authenticity. Her relationships—with her family, ex-boyfriend, and new love—reveal her capacity for forgiveness and growth.

Bennett Fox

Bennett is the quintessential alpha male—confident, creative, and competitive. Beneath his bravado lies a man scarred by guilt over a tragic accident that claimed his best friend, Sophie, and left him responsible for her son, Lucas. Bennett's fear of intimacy and self-doubt drive his initial antagonism toward Annalise, but her compassion and tenacity break through his defenses. His arc is one of redemption, as he learns to forgive himself, open his heart, and prioritize love over ambition. Bennett's humor, vulnerability, and unwavering loyalty make him a complex and compelling partner for Annalise.

Lucas

Lucas is Bennett's godson and the son of his late best friend, Sophie. Orphaned and living with a difficult grandmother, Lucas looks up to Bennett as a father figure. His presence in the story grounds Bennett and provides a lens through which themes of family, loss, and healing are explored. Lucas's journey mirrors Bennett's, as both learn to navigate grief, forgiveness, and the meaning of home. His relationship with Annalise adds warmth and depth to the evolving family dynamic.

Sophie

Sophie's death is the catalyst for much of Bennett's emotional turmoil. Her journals and memory haunt the narrative, shaping Bennett's guilt and Lucas's longing. Sophie's love for Bennett, revealed posthumously, adds layers of complexity to his relationships and decisions. She represents the enduring impact of loss and the possibility of healing through remembrance and love.

Jonas

Jonas is the boss who oversees the merger and the competition between Annalise and Bennett. He serves as a voice of reason, mediator, and occasional comic relief. Jonas's guidance and support are instrumental in helping both protagonists navigate the challenges of the workplace and their personal lives. His belief in their potential, even when they doubt themselves, is a stabilizing force.

Madison

Madison is Annalise's best friend and confidante. As a food critic, she provides comic relief and sage advice. Madison's unwavering support helps Annalise process her feelings for Bennett, confront her fears, and make difficult decisions. Her presence highlights the importance of friendship and chosen family in overcoming adversity.

Andrew

Andrew is Annalise's ex-boyfriend, whose ambivalence and emotional distance set the stage for her journey of self-discovery. His reappearance tests Annalise's resolve and forces her to confront what she truly wants in a partner. Andrew's inability to commit contrasts sharply with Bennett's eventual willingness to fight for love.

Margo and Matteo

Annalise's mother and stepfather provide a loving, if sometimes meddlesome, family environment. Their support and acceptance of Bennett help bridge the gap between rivalry and romance. Margo's matchmaking and Matteo's wisdom offer comic relief and emotional grounding, reinforcing the theme of family as both a source of strength and complexity.

Fanny

Fanny is Lucas's grandmother and Sophie's mother. Her bitterness and resentment toward Bennett stem from grief and blame over Sophie's death. Fanny's antagonism provides a foil to Bennett's efforts at redemption and underscores the long-lasting effects of trauma. Her eventual passing allows for healing and the formation of a new family unit.

Tobias

Tobias is a rival creative director and a potential love interest for Annalise. His presence in the story highlights the professional stakes and the temptation to compromise integrity for advancement. Tobias's interactions with Annalise and Bennett serve as a catalyst for self-reflection and growth, forcing both protagonists to define their values and priorities.

Plot Devices

Dual POV and Alternating Narration

The novel employs a dual point-of-view structure, alternating between Annalise and Bennett's perspectives. This device allows readers to experience the rivalry, attraction, and emotional growth from both sides, deepening empathy and understanding. The alternating narration heightens dramatic irony, as each character's internal struggles and misconceptions are revealed to the reader before they are to each other.

Enemies-to-Lovers Trope

The central plot device is the classic enemies-to-lovers arc, where professional competition and personal animosity give way to mutual respect, attraction, and ultimately love. The trope is subverted by layering in genuine emotional wounds, ethical dilemmas, and high-stakes career ambitions, making the transition from rivals to partners both believable and hard-won.

Symbolic Pranks and Office Antics

The ongoing prank war—parking tickets, office sabotage, and witty banter—serves as both comic relief and a metaphor for the characters' emotional defenses. Each prank is a form of flirtation, a way to test boundaries, and a means of expressing feelings that words cannot. The humor softens the intensity of the rivalry and paves the way for deeper connection.

Past Trauma and Redemption

Both protagonists are shaped by past trauma—Annalise's failed relationship and Bennett's guilt over Sophie's death. The narrative uses flashbacks, confessions, and the discovery of Sophie's journals to explore the lingering effects of loss and the possibility of redemption. Healing is depicted as a gradual, nonlinear process, requiring honesty, forgiveness, and the willingness to risk vulnerability.

High-Stakes Professional Competition

The competition for the creative director position is the engine of the plot, forcing Annalise and Bennett to confront their ambitions, ethics, and priorities. The structure of three client pitches, judged by the board, creates a ticking clock and escalating tension. The professional stakes mirror the personal stakes, as both must decide what they are willing to sacrifice for love and success.

Foreshadowing and Parallelism

The novel employs foreshadowing through recurring motifs—parking tickets, family dinners, and references to past relationships. The parallel journeys of Annalise and Bennett, both haunted by loss and striving for connection, reinforce the theme of second chances. The resolution of their rivalry and romance is seeded early, making the eventual union feel both surprising and inevitable.

Analysis

We Shouldn't is more than a witty enemies-to-lovers office romance; it is a nuanced exploration of how ambition, trauma, and vulnerability shape our capacity for love. Vi Keeland uses sharp dialogue, humor, and alternating perspectives to create characters who are both flawed and deeply sympathetic. The novel interrogates the myth of the "perfect" partner, showing that true intimacy requires honesty, forgiveness, and the courage to confront one's own demons. The professional rivalry is not just a backdrop but a crucible that tests the protagonists' values and priorities. The story's emotional arc—from animosity to trust, from guilt to redemption—mirrors the journey many face in balancing career and personal fulfillment. Ultimately, the novel argues that love is not about finding someone who completes you, but about choosing to build something real and lasting with another imperfect human. The lessons are clear: vulnerability is strength, forgiveness is essential, and sometimes, the person you shouldn't fall for is exactly the one you need.

Last updated: October 20, 2025