Between The Wines Book Club
Rocking Books

The Boyfriend is Unbecredifabulous

Plot Summary - “unbecredifabulous.”

The Boyfriend is a psychological thriller that alternates between the past and present, revealing a decades-long cycle of violence, stalking, and twisted obsession.


The Present: The Obsession and The Frame

Sydney Shaw, a 34-year-old woman in Manhattan, meets and falls for Dr. Tom Brown (Brewer), a handsome medical examiner. After a rapid, wonderful courtship, Sydney becomes unnerved by a series of red flags: Tom uses a burner phone, lies about his last name, and she finds a scrunchie belonging to her deceased neighbor, Bonnie.

The plot darkens when Sydney’s ex-boyfriend, Detective Jake Sousa, reveals that Bonnie’s murder is linked to a serial killer. Tom quickly becomes the prime suspect. However, Sydney discovers evidence linking her friend Gretchen’s fiancé, Randy, to the murder.

The climax occurs when Sydney, Tom, Gretchen, and Randy are all together. Tom appears and calls Gretchen by the name “Daisy,” revealing a terrifying connection. It is then revealed that Gretchen—who used the high school nickname Daisy—has been stalking Tom and murdering the women he dates (including Bonnie) in the hopes that they can be together. Tom calls the police to report Randy’s murder (implying Gretchen killed Randy) before accepting Gretchen’s offer to run away with her, admitting he can’t live without her.

The Past: The Origin of Violence

In a parallel, past storyline, Tom Brewer is a troubled high school student obsessed with his crush, Daisy Driscoll. He witnesses constant domestic abuse by his father and fantasizes about killing him.

  • First Murders: After his father jokes about sexually assaulting Daisy, Tom snaps, stabbing his father and slitting his throat. His friend Slug helps him dispose of the body. When Daisy’s best friend, Allison, threatens to expose Tom after seeing him kiss a missing student, Brandi Healy, Allison vanishes. Allison’s mutilated body is later found in the river.

  • Daisy’s Confession: Tom meets Daisy and discovers she killed Slug to frame him for the murders. She confesses she killed Allison to protect Tom and killed Brandi out of jealous jealousy after Brandi kissed Tom. Horrified, Tom vows to keep Daisy’s secret, cementing their toxic, violent bond.

Conclusion

One month later, Sydney receives a lock of hair and a note from Tom promising that her aggressive first date, Kevin, will never bother her again. She chooses not to report this information to Detective Sousa. The novel concludes with the chilling implication that the deeply damaged Tom and Gretchen (Daisy) have continued their cycle of violence together, protected by their shared secrets and mutual obsession.

“A Diet Coke?” Kevin seems affronted. “That’s boring. Get a real drink.”

Character Analysis

Sydney Shaw

is the novel’s protagonist and narrator of the “Present Day” plotline. She is a 34-year-old woman whose defining characteristic is her desire to be married and have a family, a goal that she places at the center of her life. This sincere romantic ambition, however, makes her an unreliable judge of character and dangerously vulnerable.

Vulnerability: Her desire to find “the One” causes her to dismiss numerous red flags about her new boyfriend, Tom. Even when she discovers he lied about his name and uses a burner phone, she is willing to move forward, underscoring the theme of Navigating Safety Risks in the Dating World.

Perception: Her neutral physical description (brown hair with blonde streaks, intriguing gray eyes) contrasts with the highly polarized descriptions of the other women in Tom’s life, suggesting she is an everywoman who is ill-equipped to deal with the extreme violence that surrounds her.

Tom Brewer

is a primary narrator who appears in both timelines, driving the suspense. Physically handsome and seemingly controlled, he is defined by a hidden, lifelong obsession with violence and blood.

Dark Intellect: The “Before” chapters reveal Tom’s high school self, a brilliant student who fuels his violent fantasies by reading medical textbooks and obsessing over the physiological details of death. This knowledge foreshadows his career as a medical examiner.

Moral Breaking Point: His escalating violent fantasies cross the line into action when he kills his abusive father. This act is the pivotal moment in his moral decline, which he shockingly describes as “one of the best moments of [his] life.”

The Unwitting Tool: As an adult, he keeps his murderous impulses contained, making him a compelling love interest. He functions as a red herring for the murders he didn’t commit, but ultimately runs away with the true killer, Gretchen (Daisy), bonded by their shared attraction to violence and their need to escape societal pressures.


Gretchen “Daisy” Driscoll

(childhood nickname Daisy) is the novel’s primary antagonist and the mastermind behind the present-day murders. The intentional disparity in her descriptions obscures her identity until the climax.

The Facade: The teenage “Daisy” is presented as an angelic, golden-haired pillar of the community whom Tom idealizes as “perfect.” This contrasts sharply with the “Present Day” Gretchen, whom Sydney finds less attractive.

The True Killer: The novel’s twist reveals that Daisy is a highly sophisticated, manipulative, and violent killer. She committed three murders—her classmate Brandi (out of jealousy), and her childhood friend Allison and her fiancé Randy (to protect her secret). Her murderous actions are rooted in a desire to maintain her control over Tom, demonstrating her ultimate obsession.


Jake Sousa

is a detective, Sydney’s ex-boyfriend, and an eventual love interest. He is characterized by his initial obsession with work, which destroyed his previous relationship with Sydney.

The Transformation: At the start, Jake is defined as the detective who prioritizes his job above all else. However, as Sydney’s life is put in increasing danger, Jake begins to realize his true priorities. He becomes protective and attentive, ultimately vowing to prioritize their relationship, signifying his character growth and making him “the One” at the novel’s close.


Kevin

is a secondary antagonist who stalks Sydney after a bad Cynch date. He is physically described in monstrous terms (“slimy lips,” “spindly fingers”) and embodies the immediate, physical threat that underscores the theme of Misogyny and Safety Risks in the Dating World. His behavior escalates from implicit criticism (“negging”) to overt assault, reflecting the violence women face in dating. His final, unresolved note to Sydney shows the persistent danger he poses.


Slug

“Slug” is Tom’s childhood best friend and an important supporting character/red herring in the “Before” chapters. He is characterized by his anti-social behavior (smoking, drinking, eating bugs), which is explicitly linked to Cycles of Violence and Neglect in Families (his elderly parents could not “deal with him”). His physical description closely matches Kevin’s, leading readers down a false path to obscure the true killer’s identity. Slug is a victim of his environment and dies at Daisy’s hands when she frames him for two murders.

Symbols

Cynch

the fictional dating app, is a recurring motif that highlights Navigating Misogyny and Safety Risks in the Dating World. Although marketed as “the most popular dating app,” it is primarily emphasized as a tool used by predatory characters to monitor and stalk victims.

Duplicity and Access: The app is a breeding ground for duplicity; users like Kevin can easily create new profiles and continue to harass blocked victims, showing a critical lack of protection for users.

Need for Caution: Sydney’s history of “bad dates” and her initial encounter with the aggressive Kevin demonstrate the necessity of extreme caution in online dating. Her fear that “half the guys on Cynch are just Kevin in disguise” reflects the larger, pervasive threat of misogyny and predatory behavior.


Bonnie’s Scrunchie

is a symbol of individuality in the face of anonymity on dating apps, and it acts as a touchstone for reality in the investigation.

Signature Identity: The scrunchie is Bonnie’s signature style element, emphasizing her unique personality against the backdrop of online anonymity. Her death, the inciting incident, makes the accessory a poignant reminder of her lost life.

Catalyst for Action: Sydney’s discovery of a black scrunchie in Tom’s apartment is the catalyst for the plot’s major reveal, linking Tom to Bonnie’s murder.

Touchstone of Truth: The scrunchie ultimately acts as a touchstone for reality, forcing Sydney to trust her own instincts over Tom’s excuses. Her subsequent action of stealing Tom’s water bottle for fingerprints and escaping her apartment is a direct result of the scrunchie affirming her late friend’s importance.


Tom and Daisy Buchanan

The central romantic pairing of Tom Brewer and Gretchen/Daisy is an eerie echo of Tom and Daisy Buchanan from F. Scott Fitzgerald’s The Great Gatsby, reinforcing the theme of violence and amoral wealth.

Shared Traits: Like the Buchanans, Tom Brewer and Gretchen/Daisy are presented as a pair of “careless people” who use their charm (Tom’s doctor prestige, Daisy’s ethereal beauty) to hide their brutality and violence.

Shared Arc: Their plot trajectory mirrors the Buchanans’ arc: both couples run away together after tragedy strikes to avoid the consequences of their actions, relying on their privilege and lack of remorse. The literary allusion evokes the inherent violence and ultimate amorality of their relationship.

Navigating Misogyny and Safety Risks in the Dating World

The novel portrays the contemporary online dating landscape as a uniquely dangerous space for heterosexual women, rife with misogyny and safety risks.

Online Deceit and Stalking: The app Cynch is depicted as a tool for deceit, allowing predatory men like Kevin to mask their true appearance and intentions. Despite being blocked, Kevin easily uses new profiles to stalk and harass Sydney, exposing a critical lack of protection for users.

Entitlement and Assault: Characters like Kevin embody a misogynistic entitlement, believing they are due a woman’s time and body. Kevin’s escalating behavior, from criticizing Sydney’s body (“negging”) to demanding a kiss and attempting assault, highlights the violence women encounter. Even when Sydney threatens to call the police, Kevin continues his harassment, reflecting his belief that he is entitled to her attention.

Systemic Misogyny: Randy, Gretchen’s boyfriend, exemplifies how men in positions of power (a superintendent) can use their access to abuse women (going through tenants’ underwear drawers) and evade consequences, despite a history of assault charges. This reinforces the systemic nature of the violence women face in the dating world.


Cycles of Violence and Neglect in Families

The novel suggests a direct link between childhood exposure to violence and neglect and the violent tendencies exhibited in adulthood, cementing a dark cycle of abuse.

Inherited Violence: Tom Brewer’s violent fantasies are rooted in his childhood experience of his father’s alcoholic abuse of his mother. Though Tom insists he is “nothing alike” his father, he was implicitly taught that romantic relationships are linked to violence. His murder of his father, which he finds exhilarating, is a pivotal moment where he crosses the line from thought to action.

Slug’s Neglect: The secondary character, Slug, embodies the effects of simple parental neglect. His anti-social behavior is directly attributed to his parents’ lack of care, implying that neglect is as corrosive as overt violence.

Perpetuating the Cycle: The novel ends with Tom and Gretchen/Daisy—whose own murders were acts of obsessive love and control—running away together to “have a family.” This suggests that their mutual attraction to violence and their decision to embrace their darkest impulses will ensure the cycle of violence continues into the next generation. Tom’s murder of Kevin, an act of protecting Sydney from abuse, adds a chilling moral twist, but does not break the cycle of violence itself.


The Pressure of Social Expectations

The novel critiques the intense social pressure young women like Sydney and her friends face to find a partner, marry, and have children, which leads them to make choices against their self-interest.

Urgency and Scarcity: Sydney and her friend Bonnie approach dating with an intense sense of urgency and scarcity, feeling they must date constantly to achieve their goal before time runs out. The narrative uses the trope of the ticking biological clock (via Sydney’s mother’s increasingly desperate phone calls) to amplify this pressure.

Ignoring Red Flags: This social pressure incentivizes Sydney to rationalize warning signs and “a number of red flags” in Tom’s behavior. She is willing to overlook obvious danger because she has convinced herself that Tom “could be the One.”

Reifying Traditional Roles: Even when Sydney acknowledges a man’s misogyny or criminal past (like with Randy), she occasionally undermines her own awareness by still seeing marriage as the “happy ending” for her friend. This highlights how social expectations can force women to reify traditional, often problematic, gender roles and expectations.

Bookclub Questions

Initial Impressions

  1. How does The Boyfriend compare to other psychological thrillers by Freida McFadden, such as The Housemaid or The Coworker? Did the plot twists and pace meet your expectations for her writing, and would you recommend this novel to a fan of the genre?
  2. Thrillers rely heavily on suspense and unpredictable twists. Did the plot and the eventual reveal of the killer surprise you? Were you emotionally invested in discovering who murdered Bonnie?

Personal Reflection and Connection

  1. Trust and Occupation: Tom’s profession as a doctor initially makes him seem trustworthy. Why do you think some occupations carry inherent associations of trustworthiness (or suspicion)? What is an occupation you consider to be highly trustworthy, and one you tend to be suspicious of?
  2. Childhood Trauma: Tom’s character is shaped by witnessing abuse in his childhood. Why do you believe childhood experiences are so formative? Do you think someone can fully recover from early trauma without it negatively impacting their adult personality?
  3. Jealousy and Control: Jealousy is revealed as the core motive for Bonnie’s murder. Why is jealousy such a powerful, destructive emotion? What situations or characteristics tend to trigger feelings of jealousy in you?
  4. Destructive Impulses: Tom attempts to cope with his violent impulses by killing men he believes “deserve it” (like his father and Kevin). Do you believe people with destructive tendencies can successfully channel and control those urges? What are some healthy ways to manage a desire to harm others?

Societal and Cultural Context

  1. Fear of Male Violence: The novel ultimately subverts the expectation that the killer is male, but the looming threat of male violence is crucial to the plot. How do you think the pervasive fear of male violence shapes women’s experiences and caution in the contemporary world?
  2. Dating App Culture: The novel reveals the potential dangers and duplicity of dating app culture. Why do you think dating apps have become so prevalent? What are the key pros and cons of relying on this technology to find romantic partners?

Literary Analysis

  1. Dual Plot Structure: The novel uses a dual structure (Sydney’s present-day POV and Tom’s past-day POV). How did this structure impact the suspense and drama, particularly in confusing the reader about who the real killer was? Did you prefer one storyline over the other?
  2. The Romantic Rescuer Trope: Tom reflects the trope of the “romantic rescuer” twice in the novel. How did this cliché affect Sydney’s initial impression of him and her attraction, leading her to overlook serious red flags?
  3. Blood Motif: Discuss the motif of blood in the novel (e.g., Sydney’s blood-clotting disorder, Tom’s fixation on blood/murder). How does this motif relate to the novel’s mood and its themes of violence and hidden identity?
  4. Justice and Accountability: Is Sydney justified in not reporting Kevin’s murder at the end of the novel? Do you believe justice is served by the conclusion, given that the two murderers (Tom and Gretchen/Daisy) run off together?

Creative Engagement

  1. The Gatsby Allusion: The names “Tom” and “Daisy” allude to The Great Gatsby. Choose one scene or quotation from Fitzgerald’s novel and discuss how it illustrates themes of amoral wealth, violence, or obsession similar to those explored in The Boyfriend.
  2. Literary Dating Profile: Create a mock dating app profile for a famous literary “boyfriend” (e.g., Romeo, Mr. Darcy, Heathcliff). How would you use a dating profile to illustrate both the allure and the limitations/dark side of that male character?

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