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Heartbreakers (2001) Plot Summary & Timeline

Heartbreakers (2001) movie poster

Heartbreakers is a 2001 comedy and romance film directed by David Mirkin, running 2 hours 3 minutes. This page retells the whole story in 452 words (about 2 minutes to read) and covers 15 key events in order, 3 characters, where and when it is set and 3 themes. Looking for the cast, ratings and where to stream it? See the movie page for Heartbreakers.

to read the plot summary
2 min
key events in the timeline
15
characters profiled
3
themes explained
3
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Heartbreakers (2001) movie poster
Released
Runtime
2h 3m
Director
David Mirkin
Genres
Comedy, Romance, Crime
Original language
English
No spoilers

What Is Heartbreakers About?

The premise of Heartbreakers in 337 words, with nothing given away. The full story follows below.

In the glitter‑laden world of high‑society weddings and upscale cocktail parties, a seasoned swindler and her eager apprentice make their living by turning romance into profit. Max carries the confidence of a veteran con artist, her poise polished by years of meticulously staged courtships, while her daughter, Page, supplies the youthful daring and quick‑witted charm that keep the schemes fresh. Together they move through glamorous circles with a blend of sharp humor and calculated grace, treating each new affluent encounter as both a game and a lesson in survival.

The duo’s dynamic hinges on a delicate balance of control and rebellion. Max exerts a protective, almost maternal grip over every detail of Page’s life, dictating everything from her wardrobe to her habits, all in the name of keeping their operation tight and their emotions in check. Page, hungry for independence and larger scores, pushes against those restraints, dreaming of a life where she can set her own terms rather than merely follow her mother’s script. Their interactions crackle with witty banter and underlying tension, giving the partnership a rhythm that feels as unpredictable as it is synchronized.

At the heart of their enterprise lies a familiar pattern: the mother marries a wealthy suitor, while the daughter flirts and extracts the final cut. This elegant dance of deception, played out against a backdrop of luxury hotels, upscale restaurants, and the ever‑watchful eyes of the elite, provides both the thrill of the con and the comedy of their constant near‑captures. Yet the allure of their latest mark promises a fresh challenge—a target whose sharp perception threatens to expose the careful choreography they have perfected.

As the film unfolds, the audience is invited to savor the stylish cat‑and‑mouse game, the sparkling dialogue, and the bittersweet question of whether a mother’s devotion can ever truly protect a daughter from the consequences of a life lived on the edge. The tone remains a lively mix of comedy and romance, hinting at deeper emotional stakes without revealing the outcomes of their daring gambits.

Full plot

What Happens in Heartbreakers?

The complete story of Heartbreakers, from the first scene to the last, in 452 words (about 2 minutes). Spoilers throughout. Names in the text link to 3 cast member pages.

Spoilers ahead

Max, portrayed by Sigourney Weaver, along with her daughter Page Conners, played by Jennifer Love Hewitt, form a cunning duo of con artists. They set their sights on Dean Cumanno, a small-time auto-body shop owner, with a meticulously crafted scheme that they have executed many times before. The plan involves Max marrying Dean and then sexually teasing him during their wedding dinner, allowing for a series of distractions, including her dancing with the busboy, postponing their honeymoon. On their wedding night, Max feigns a fainting spell, avoiding any intimacy and leading to a quick divorce. Meanwhile, Page cunningly poses as Dean’s secretary, further entrapping him in a situation that would justify Max’s request for a hefty divorce settlement.

The con goes off without a hitch, securing Max a $300,000 settlement thanks to the intervention of their divorce attorney, Mr. Surpin, played by Carrie Fisher. Under pressure from Surpin, Dean is threatened with the exposure of his shady automotive business, compelling him to comply. However, Max holds a tight grip on Page’s life, controlling every aspect—including what she can eat and even whether she can smoke. Frustrated by their small-time hacks, Page dreams of going for bigger targets, especially when they find themselves under scrutiny from the IRS, led by Gloria Vogal, portrayed by Anne Bancroft. The agency reveals that they owe an astonishing $247,811 in back taxes due to Max’s negligence over the last seven years.

Faced with a ticking clock to settle their debts, Page reluctantly teams up with Max for one final heist, targeting William B. Tensy, a tobacco baron played by Gene Hackman. Their plan takes them to Palm Beach where, after a ruse involving a faux injury to obtain a luxury hotel suite, they set in motion their scheme to fleece Tensy. However, complications arise as Page encounters Jack, a bartender who captures her attention, leading her to develop genuine feelings. Caught between her mother’s controlling advice and her own desires, Page finds herself in a web of deceit and emotional turmoil.

As the story unfolds, the duo faces unexpected challenges, from Jack’s accidental interference to Tensy’s unexpected demise. This culminates when Jack’s infidelity shakes Page to her core, and secrets involving Max’s manipulative past threaten to unravel the tenuous bonds of trust between mother and daughter. Ultimately, Max must confront her protective instincts and the unintended damage they have inflicted on Page’s life. In a poignant climax, Max realizes that her efforts to guard Page from life’s hurts have backfired, leading to a tearful reconciliation as Page chooses to reclaim her life and her future with Jack. Meanwhile, Max and Dean find an unexpected connection, setting the stage for new schemes and the promise of adventure ahead.

Timeline

Heartbreakers Timeline: Every Key Event in Order

15 key events in the order they happen, from “Introduction of Max and Page” to “New Beginnings”.

  1. 1

    Introduction of Max and Page

    Max, a cunning con artist, teams up with her daughter Page to execute a series of elaborate scams. They share a close bond and have mastered the art of deception together, with a focus on small-time targets.

  2. 2

    Setting Sights on Dean

    The duo sets their sights on Dean Cumanno, a small-time auto-body shop owner, crafting a detailed scheme designed to swindle him. Their plan involves Max marrying Dean to full execute their manipulations.

  3. 3

    The Wedding Dinner

    During the wedding dinner, Max employs a series of distractions, including dancing with a busboy, to further instigate chaos. This is all part of their plan to keep Dean off balance and unable to catch onto their deception.

  4. 4

    The Wedding Night

    On their wedding night, Max feigns a fainting spell to avoid intimacy with Dean. This act further enables her to expedite the divorce process as she swiftly orchestrates their separation.

  5. 5

    The Divorce Settlement

    Thanks to their unscrupulous divorce attorney, Mr. Surpin, Max secures a $300,000 settlement without any complications. Dean, facing threats of exposure regarding his dodgy automotive dealings, has no choice but to comply.

  6. 6

    Control Over Page

    Max exerts tight control over Page’s life, regulating her choices regarding food and habits. This controlling behavior sparks frustration in Page, who yearns for independence and bigger targets.

  7. 7

    IRS Scrutiny

    Under the scrutinizing gaze of the IRS, represented by Gloria Vogal, they discover a staggering amount of back taxes owed due to Max's negligence over seven years. This revelation forces Page and Max to reevaluate their future.

  8. 8

    Planning the Final Heist

    With an urgent need to settle their debts, Page reluctantly agrees to partner with Max for one last con. They target William B. Tensy, a wealthy tobacco baron, hoping to execute a successful scam.

    Where:Palm Beach

  9. 9

    Faux Injury Scheme

    In Palm Beach, they orchestrate a ruse involving a faux injury to secure a luxury hotel suite. This deception is pivotal to their plan to fleece Tensy effectively, showcasing their con artist skills.

    Where:Palm Beach

  10. 10

    Page Meets Jack

    While executing the con, Page meets Jack, a bartender who captivates her. As she develops genuine feelings for him, Page finds herself torn between her mother's controlling ways and her burgeoning desires.

Show the other 5 events of Heartbreakers
  1. 11

    Complications Arise

    Unexpected challenges arise when Jack inadvertently disrupts their plans, complicating the heist. Additionally, Tensy faces an untimely demise that threatens the whole scheme, shaking their confidence.

  2. 12

    Jack's Infidelity

    Page's world is rocked when she discovers Jack's infidelity, leading to a profound emotional crisis. This betrayal highlights the complexities of her relationships and the impact of her mother's influence.

  3. 13

    Confrontation with Max

    Secrets regarding Max's manipulative past surface, creating tension between mother and daughter. The confrontation forces Max to confront the consequences of her overprotectiveness and its damage on Page's life.

  4. 14

    Tearful Reconciliation

    In the climax, Max and Page share a tearful moment of reconciliation, realizing the need for trust and understanding. Page decides to reclaim her life, asserting her independence while coming to terms with her feelings.

  5. 15

    New Beginnings

    With unresolved feelings for Dean, Max finds an unexpected connection with him. The stage is set for new schemes and adventures ahead, marking a fresh start for both Max and Page as they embrace life's unpredictability.

Characters

Who Are the Main Characters in Heartbreakers?

3 characters, among them Max Conners, Page Conners and Dean Cumanno: who each one is and the part they play in the story. 2 of them link to the actor’s page.

  • Sigourney Weaver as Max Conners in Heartbreakers

    Max Conners

    Played by Sigourney Weaver

    Max is a savvy and charismatic con artist who uses her charm and cunning to swindle men out of their money. Her controlling nature reveals her deep-seated fears of vulnerability, particularly towards her daughter. Throughout the film, she grapples with the consequences of her manipulative behavior on her relationship with Page.

    • 💃 Manipulation
    • 🦸‍♀️ Control
  • Jennifer Love Hewitt as Page Conners in Heartbreakers

    Page Conners

    Played by Jennifer Love Hewitt

    Page is a young and ambitious woman caught between her mother's manipulative ways and her growing desire for independence. As she assists in the con, she starts to question her moral compass and develops romantic feelings that challenge her existing loyalties. Her journey represents a quest for identity amidst familial expectations.

    • 🌱 Independence
    • 💔 Conflict
  • DC

    Dean Cumanno

    Dean is depicted as an unsuspecting and naive auto-body shop owner who becomes the target of Max and Page's con. His character arc reveals the dangers of naivety and the impact of deceit on personal relationships. He struggles with the fallout of his involvement in Max's schemes.

    • 💼 Naivety
    • 🔄 Betrayal
Setting

Where and When Is Heartbreakers Set?

Heartbreakers is set in Palm Beach. Here is why the place matters to the story.

Where

Palm Beach

Palm Beach is known for its luxurious hotels, upscale shopping, and beautiful beaches. This affluent area serves as a backdrop for the con artists' final heist, showcasing opulence and deception intermingled. It's a place where wealth meets intrigue, amplifying the stakes of the duo's intricate scheme.

  • 🏖️ Beach
  • 💼 Business
Themes

What Are the Themes of Heartbreakers?

3 ideas the story keeps returning to, among them Conspiracy, Family Dynamics and Greed.

  1. 01

    Conspiracy

    The theme of conspiracy pervades the film as mother and daughter navigate the complexity of their deceitful lives. Their intricate schemes highlight the lengths to which they go for financial gain, revealing the moral ambiguity of their actions. It also examines the impact of such unethical choices on their personal relationships.

  2. 02

    Family Dynamics

    The relationship between Max and Page serves as a central theme, marked by control, manipulation, and ultimately reconciliation. While Max intends to protect Page, her methods lead to emotional strife and turmoil. The film explores how familial bonds can be both a source of strength and conflict.

  3. 03

    Greed

    Greed is a driving force behind the actions of the characters as they pursue wealth through deceitful means. The film emphasizes the allure of quick riches and the consequences that arise from greed-driven endeavors. It draws attention to the moral cost associated with their relentless quest for money.

Tone & mood

What Kind of Film Is Heartbreakers?

Light in tone, with fast pacing and a moderate story, going by the plot summary.

Tone
Light
Pacing
Fast
Story
Moderate
Intensity
Medium
Ending
Happy

A slick, fast-paced con-artist comedy that feels like a playful caper, balancing romantic entanglements and high-stakes deception with a light, energetic tone and a satisfyingly happy resolution.

  • playful
  • deceitful
  • romantic
  • conflicted
  • energetic
  • slick
  • con artists
  • mother daughter relationship
  • romantic deception
  • financial scam

Content notes: infidelity.

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Read next

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6 films close to Heartbreakers in story and themes that have a full plot summary here: Heartbreaker (2010) and The Heartbreak Kid (2007) lead.

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FAQ

Heartbreakers Plot Questions

5 quick answers about Heartbreakers, taken from the plot summary, character guide and setting on this page and the film’s credits.

What is Heartbreakers about?

In the glitter‑laden world of high‑society weddings and upscale cocktail parties, a seasoned swindler and her eager apprentice make their living by turning romance into profit.

Read the full plot summary

When and where does Heartbreakers take place?

Heartbreakers is set in Palm Beach. Palm Beach is known for its luxurious hotels, upscale shopping, and beautiful beaches. This affluent area serves as a backdrop for the con artists' final heist, showcasing opulence and deception intermingled.

The setting explained

Who are the main characters in Heartbreakers?

The story follows Max Conners (played by Sigourney Weaver), Page Conners (played by Jennifer Love Hewitt) and Dean Cumanno.

All the characters

What are the main themes of Heartbreakers?

The summary picks out 3 themes: Conspiracy, Family Dynamics and Greed.

The themes explained

Who directed Heartbreakers?

Heartbreakers (2001) was directed by David Mirkin and runs 2 hours 3 minutes.

David Mirkin’s films

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