Feel free to pick and choose — you don’t need to use all of these in one sitting unless your book club is in the mood for a full Connecticut reckoning.

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CHARACTERS: WHO LET THESE PEOPLE BUY SUCH EXPENSIVE HOUSES?
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  1. Anders on the Page vs Anders on the Screen
    Book-Anders is sixty, Southern, and steeped in two decades of slow-burning resentment. Film-Anders is younger, Australian (via Ben Mendelsohn), and somehow even more hapless. Did your mental image of Anders from the novel match what walked onto screen? Did you find him more sympathetic, more irritating, or just more baffling in one version vs the other — and does it matter that he’s almost impossible to fully root for in either?
  2. Ben Mendelsohn: Wrong Man or Exactly Right?
    Casting an Australian to play a Connecticut WASP in existential freefall is a bold move. Critics called Mendelsohn’s performance “magnificently off-center.” Did that off-centeredness feel like inspired casting — the slight wrongness embodying Anders’ own sense of not-quite-fitting — or did it just feel like miscasting with good acting on top? Who did you picture when you were reading?
  3. Helene: Earthy Fire in an Under-Conceived Role
    Edie Falco was praised but the role itself was criticized as under-conceived. The novel gives Helene far more interiority and time in her own point of view. Did you feel the book’s Helene, or the film’s Helene, was the more complete person? Is a Helene who mostly reacts to Anders a problem of adaptation, of genre, or of the story’s DNA?
  4. Charlie and Preston: The Two Stages of Failing Upward
    Charlie (high school, still unraveling) and Preston (post-rehab, barely holding it together) form a kind of tragic relay team — the three stages of the Connecticut man: boy, almost-adult, and man who should know better by now. Did the film give each of them enough room to be more than cautionary decorations? Which one felt most alive on screen, and which felt most alive on the page?
  5. Barbara: Romantic Interest or Holofcener Addition?
    Barbara (Connie Britton) doesn’t exist in the novel. Holofcener added her as a romantic possibility for Anders, and critics noted the addition felt like “a concession to movie convention.” Did Barbara earn her place? Did her presence soften the film’s edges in ways that helped or hurt it? And what does it say about the differences between how novels and films handle solitude that the book is comfortable leaving Anders largely without this thread?
  6. Donny: The World’s Most Uncomfortable House Guest
    Donny — Anders’ college roommate, Helene’s college boyfriend, and now the man sleeping in Anders’ old bed in Anders’ old house on Anders’ dime — is a masterpiece of situational cruelty. Did the film give Bill Camp enough to do with the role? And was the revelation (in the film) that Helene had been sleeping with Donny before the divorce landed with the weight it deserved, or did it slide past?

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PLOT SURGERY: WHAT GOT RETIRED, WHAT GOT REHIRED
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  1. One POV to Rule Them All
    Thompson’s novel rotates between Anders, Helene, and Preston — giving each their own inner weather. Holofcener’s screenplay narrows the lens almost entirely to Anders. What did you lose when Helene and Preston lost their interiority? Did the film compensate through performance, or did certain scenes feel thinner without access to what those characters were actually thinking?
  2. The Opening: Shopping as Character Revelation
    The film opens with Anders adrift in a home goods store, paralyzed by the infinite choices of solo life — a scene Holofcener invented that has nothing to do with the novel. Did this feel like the right entry point into Anders’ world? Critics called it a perfect conflation of consumerism and personal identity. Did it set up the right version of Anders, or a slightly different one than the book established?
  3. Helene’s Breast Cancer: Missing from the Film
    In the novel, Anders delayed the divorce for a year because Helene was diagnosed with and then recovered from breast cancer — a detail that makes his eventual departure feel both more cowardly and more complicated. The film drops this entirely. Did you miss it? Does removing it make Anders’ choices feel cleaner, messier, or just differently weighted?
  4. The PCP Scene: Present in Both, Differently Weighted
    Anders smoking PCP with teenage Charlie at a holiday party — which sends Charlie to the hospital and effectively detonates what’s left of Anders’ social standing — is in both versions. Compare how each handles it. Does the film earn the scene as a turning point, or does it arrive and depart without quite the accumulated dread the novel builds toward it?
  5. Preston’s Champagne Bottle on the Train Tracks
    One of the film’s quietly devastating moments: Preston, stranded, contemplates a large bottle of champagne before placing it on the train tracks instead of drinking it. A small act of self-restraint that costs nothing and changes nothing, and means everything. Did this land for you? Is this the kind of moment — tiny, specific, almost inexplicable — that film does better than prose, or that prose set up and film delivered?
  6. The Turtle: More Screen Time Than Several Humans
    Charlie’s pet turtle — which he asks Anders to look after when he’s on the run from rehab — received genuine critical attention as a symbol that’s both funny and quietly devastating. Did the turtle work for you as a plot device? As a symbol? As a living creature whose fate you genuinely worried about? And be honest: at any point did you care more about the turtle than about Anders?

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TONE & VIBE: IS THIS A COMEDY? A TRAGEDY? A VERY NICE HOUSE?
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  1. Comedy-Drama: Where Does the Needle Point?
    Both versions walk the wire between funny and sad — sometimes in the same sentence. The novel has Thompson’s dry, precisely observed prose doing the balancing act. The film has Holofcener’s direction and Mendelsohn’s face. Which version landed the comedy-drama tonal balance better for you? Were there moments where one version made you laugh that the other played straight, or went sad where the other found absurdity?
  2. Connecticut as Setting: State of Mind or Just Real Estate?
    The title itself is a centuries-old nickname for Connecticut — coined as a compliment to its stability and long since curdled into a synonym for its conformity. How much did each version make you feel the weight of that place: the money, the treadmill, the unspoken rules about what a life is supposed to look like? Did the film’s visual Connecticut — the manicured lawns, the Range Rovers at the station, the plastic-wrapped boats in winter — match or enhance the novel’s version of the place?
  3. The Holofcener Signature vs the Thompson Novel
    Holofcener is known for films about “compulsively self-sabotaging women” — and this is her first adaptation, and her first film centered on a man. Did the film feel like a Holofcener movie wearing Thompson’s story, or like a genuine merger of two sensibilities? Where did you feel Holofcener’s hand most strongly? Where did the novel’s voice come through? Are there places where they felt at odds?

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THEMES: HABITS, FREEDOM, AND THE THINGS MONEY CAN’T FIX (BUT KEEPS TRYING)
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  1. The Great Midlife Retirement and What It Actually Got Him
    Anders quits his job and leaves his marriage in search of “freedom” — and finds himself decorating a condo and having joyless sex with strangers. The novel spends more time inside his original reasoning; the film is arguably harsher about the gap between his philosophy and his practice. Which version made you angrier at him? Which made you sadder for him? And did either version make you understand what he was actually looking for?
  2. “You’re Supposed to Be Happy Now”
    Helene delivers this line to Anders — half accusation, half baffled observation — and it lands like a small verdict on the entire story. Did either version explore what happiness was actually supposed to look like for someone like Anders? Or is the novel/film’s point that happiness was always the wrong category, and he mistook freedom for it?
  3. Class, Wealth, and the Performance of Conscience
    Anders quits finance on moral grounds — he can’t stomach the “monstrous greed” — and then lies at a party about doing charitable work “for diseases, on the cancer spectrum.” Both versions use this kind of hypocrisy as a recurring joke with a painful undertow. Did the film sharpen or soften the class critique? Is there a version of this story that actually lets Anders’ principles be taken seriously, or does the story fundamentally not believe him?
  4. The Three Stages of the Connecticut Man
    Charlie (still capable of destruction), Preston (capable of just barely not destroying himself), and Anders (capable of destruction while being old enough to know better) form a generational mirror. Did both versions make you feel the sadness of that relay — that each generation seems to repeat the same failures in slightly different clothing? Or did one version make the parallel feel forced?
  5. Helene’s Affair: The Moral Scorecard Nobody Wins
    The film reveals that Helene had been seeing Donny while she and Anders were still married. This complicates the easy reading of Anders as the sole villain of the divorce. Did this revelation change how you felt about Helene? Does it let Anders off the hook, add another hook, or just confirm that the whole situation is a web of people making bad choices and calling it something else?

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PAGE VS SCREEN: WHO UNDERSTOOD THESE PEOPLE BETTER?
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  1. Scenes That the Film Nailed
    Name one moment where Holofcener’s film did something the novel couldn’t: a glance, an image, a scene that only works because you can see it. The winter boats wrapped in plastic like maritime ghosts. Anders’ face in a store full of things he doesn’t need. The strip club bathroom where two people start something tentative. Which visual moment earned its place most?
  2. What the Book Did That the Camera Couldn’t
    Thompson’s prose has been called “shrewdly funny and finely observed.” What did you get from the novel’s interiority — particularly Helene’s and Preston’s points of view — that no amount of good acting could replicate? Name one scene or passage that worked better in your head than it could ever work on a screen.
  3. Episodic Structure: Feature Film or Long Short Story?
    Both versions are episodic by nature — a series of confrontations, small humiliations, and tentative gestures rather than a driving plot. Critics noted the film’s plot felt “more mechanical than organic.” Did the episodic quality work better in prose (where it reads as a literary choice) or on screen (where it can feel like a story that doesn’t quite know where it’s going)? Or did both versions make it feel intentional?

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OVERALL ADAPTATION VERDICT: HOW STEADY ARE THESE HABITS, REALLY?
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  1. Holofcener’s First Adaptation: Did She Stick the Landing?
    All of Holofcener’s previous films were original screenplays. This is her first time working from someone else’s source material. Can you feel that in the film — either in the places where it feels most alive (perhaps where she added material) or in the places where it feels most constrained (perhaps where she was being faithful to Thompson)? Does knowing it’s her first adaptation change how you evaluate it?
  2. “True to the Spirit” — Yay or Just Something People Say?
    The film keeps Thompson’s world, his title, his central characters, and his basic situation while making significant changes to point of view and adding Barbara entirely. Does the film feel true to the spirit of the novel? If you had to explain to a friend what “spiritually faithful but structurally different” means for this specific adaptation, what example would you use?
  3. What Each Version Does Best
    Give one gold star to the novel and one to the film. They don’t have to be for the same thing. (Suggested categories: Best Use of Connecticut as a Moral Indictment; Best Scene of a Man Failing to Have a Good Time; Best Turtle Symbolism; Best Performance of Someone Who Should Know Better; Best Quietly Devastating Moment Involving a Train.)
  4. Recommend: Read, Watch, or Both?
    If a friend had time for only one — which would you send them to, and why? Would your answer change if your friend loves Holofcener’s other films? If they’re more interested in the suburban-malaise theme than in any one character? If they’ve been through a late-life divorce themselves and you’re slightly worried about recommending either?
  5. Order of Operations
    Novel then film, film then novel, or just one and done? How does the order change the experience of Anders — does reading first give you a richer interior life that the film then populates with faces, or does watching first let you encounter the story without Thompson’s sardonic prose pre-loading your sympathies? And is there a case that the novel makes the film feel thin, or that the film makes the novel feel crowded?
  6. Final Club Gut Check
    On the dial from “perfect one-to-one translation” to “loosely inspired by a feeling of mild Connecticut dread,” where does this adaptation land? And the harder question: is this a story that’s better suited to the page, where Thompson’s prose can do the work that Anders himself is incapable of, or to the screen, where Ben Mendelsohn’s face can do what no amount of interiority could fully earn?

Use, tweak, or mash these questions as needed — your club, your Connecticut.