Nicole Holofcener’s debut feature film, 1996’s Walking And Talking, snuck up on me and seduced me when I was around the same age as Amelia, the film’s unmoored twentysomething protagonist, played with prickly, off-kilter charm by the writer-director’s longtime muse and spiritual stand-in, Catherine Keener. Walking And Talking used to appear on cable a lot—back then, when there were fewer channels and choices, a movie could spend months in near-daily rotation—and every time I happened across it, I would be drawn into the story at a different point, so that I saw the film many times in overlapping fragments before I ever caught it straight through.

I remember being fascinated by the seemingly meandering storyline of this female-friendship comedy. Amelia and her best friend since childhood, Laura (Anne Heche), confer on the phone about Amelia’s various failed relationships, shop for a bridal gown for Laura’s upcoming wedding, and debate whether to invest in expensive chemotherapy for the aged pet cat they once owned together as roommates. Other characters, including Laura’s fiancé Frank (Todd Field) and Amelia’s ex-boyfriend Andrew (Liev Schreiber), fold laundry, smoke pot, and rent porn videos. For a long time, I was convinced I must be continually tuning in to Walking And Talking, by sheer coincidence, just before or after the parts where something actually happened. Up until then, I had rarely seen a movie so unconcerned with conventional dramatic incident, and so confident in its conviction that ordinary quotidian experience is freighted with nuance and meaning, that there’s significance in the simple everyday transactions we engage in with other people: families, friends, exes, even the clerk at the video store.

Holofcener’s films are comedies of manners both in the literary-critical and the everyday sense. Yes, they’re trenchant explorations of the mores and folkways of the contemporary American upper-middle class. (Including, to an increasing degree as her career has progressed, issues of class privilege and class guilt. See, for example, the subplot in Enough Said about how Toni Collette’s character, Sarah, can’t fire her maid.) But Holofcener’s films are also concerned with “manners” in the more colloquial understanding of the term. She’s made five ensemble comedies in the last 18 years, and almost every one of each film’s interwoven plotlines revolves to some degree around moments of impoliteness, embarrassment, offense, apology, or regret. Once in a while, there’s a big-ticket life event—a wedding, divorce, or death—but the central drama in her movies happens in the minute interactions among characters who aren’t always fully in control of their own words and actions, people who can mean well and try hard and still screw up royally. (Like a few—okay, all—of the people I know.)

My favorite moment of Walking And Talking involves a misunderstanding between Amelia and the man she’s tentatively beginning to date, a horror-movie-obsessed video-store clerk named Bill (Kevin Corrigan). For months, they’ve been flirting as she checks out movies, but Amelia can’t quite bring herself to accept the advances of the geeky, scrawny, bespectacled Bill. In fact, she and Laura have invented a nickname for him in their private conversations: The Ugly Guy. But one night, after taking in an exhibit of horror-movie facial prostheses, Bill and Amelia finally have sex at her place. To Amelia’s surprise, Bill is a fantastic lover—a shot of her smiling at her own reflection in the bathroom mirror afterward says all the audience needs to know on that score. But while she’s in there, the phone rings, and it’s Laura, leaving an answering-machine message to ask how things went with The Ugly Guy.

This scene and its aftermath showcase everything Holofcener does best, things few other directors ever try to do at all. She can turn the audience’s sympathies on a dime, as we pivot from laughing along with Amelia and Laura’s private language to cringing at how callous it sounds to an outsider’s ears. And she trusts her actors: While the message plays, the camera remains on Bill’s face as it moves from puzzlement to hurt to angry resolve. In the space of less than a minute, we go from perceiving Bill as a quirky bit player in Amelia’s story to seeing him as the complex protagonist of his own story, vulnerable enough to be wounded by this casual insult, yet proud enough to erase the message and leave without a word about it. (Sidebar inquiry: Why has no one yet written a script with a juicy lead role for Corrigan, a superb actor who seems forever consigned to playing sad-sack sidekicks and tertiary thugs?)

For the rest of the movie, Bill ignores Amelia as she stalks him around town in comically inappropriate ways, diving behind potted plants the moment he turns around, convinced she’s the one who’s been mysteriously wronged. All the while, the audience benefits from the dramatic irony of understanding exactly why he’s pulled away. We come to see their failed romance not as a hero-and-villain story, but as a series of failed communications and unintended slights.

Nearly all Holofcener’s films expand in some way or other on the “ugly guy” story template, with the insults (usually proffered by a woman, though not always to a man) growing ever more offensive and less accidental. Many years later, in Enough Said, Holofcener built an entire romantic comedy around a similar scenario of semi-accidental betrayal: When divorced single mother Eva (Julia Louis-Dreyfus) secretly befriends Marianne (Keener), the glamorous ex-wife of her new boyfriend Albert (James Gandolfini), viewers can understand Eva’s motivations even while deploring her sneakiness. But when Albert finds out about the friendship, the perspective abruptly shifts. She’s crossed a line that he can’t forgive her for, and the audience—having enjoyed the illicit thrill of Eva and Marianne’s budding friendship ourselves—feels uneasily implicated in her shame.

In 2001’s Lovely & Amazing, Keener’s character—Michelle, a dissatisfied stay-at-home mother—can’t stop getting in trouble for speaking her mind. In the first scene, she ends an awkward transaction with a snooty shop clerk by audibly mumbling, “Bitch,” and things only get worse from there. (“You can’t just go around telling people to fuck off,” says her exasperated husband, played by Clark Gregg. “Fuck off,” she replies.) Jane, the depressed high-end clothing designer Frances McDormand plays in 2006’s Friends With Money, takes Holofcenerian lack of decorum to the next level, stomping around L.A. on a truth-telling rampage, mocking new mothers for their babies’ names and taking theatrical umbrage at every perceived slight to herself or her close circle of friends.  Jane’s eventual, humiliating fate—after throwing a public tantrum when a couple cuts in front of her on line, she walks into a plate-glass window and breaks her nose—is a comeuppance of sorts, but far from a catharsis. The movie ends with the sense that Jane, though somewhat chastened by her mishap, will continue to go through life with a disproportionate sense of entitlement and rage. Her days will always be a half-successful negotiation between what she feels she’s owed and what she owes to others—a balancing act, Holofcener seems to suggest, that isn’t unique to Jane’s particular pathology, but is a condition of modern life.

Released in 2010, Please Give—perhaps Holofcener’s most thematically ambitious film, and along with Walking And Talking and Enough Said, one of my favorites—builds its story even more explicitly around dilemmas of social decorum and the larger moral and ethical questions they mask. What is our responsibility toward our neighbors, our families, the clients in our business, the homeless people on the block? How, to get Socratic about it, are we to live with each another? Kate (Keener) and her husband Alex (Oliver Platt) are well-off vintage-furniture dealers who find the stock for their fancy Manhattan store at the estate sales of the recently deceased. They’re vultures, and they know it—especially Kate, who spends her days paralyzed by the guilt her privilege confers, unable even to volunteer at local charities without breaking down in tears. That guilt is only compounded when Kate and Alex’s down-the-hall neighbor, an elderly lady whose apartment they’ve arranged to buy after she dies, begins to decline in health. Then again, this particular old woman (Ann Guilbert) happens to be a rude, ungrateful crank to the grown granddaughters who care for her (Rebecca Hall and Amanda Peet)—once again complicating the task of judging who’s right, who’s wrong, and who owes what to whom.

Please Give ends on a scene of uneasy truce between Kate and her sulky 15-year-old daughter Abby (Sarah Steele), who’s been pestering her mother for a pair of fancy jeans that Kate regards as absurdly extravagant. At the end of a film that’s been a series of pitched battles about the proper allocation of money, time, resources, and love, Kate agrees to treat her daughter to the jeans as a gesture of reparation, which leads to an exchange that’s rare in Holofcener’s oeuvre: a completed circuit of generosity and gratitude. “Thank you,” murmurs the daughter, beaming at her reflection in the store mirror. With a tired, sad, loving smile, her mother answers, “You’re welcome.”

Dana Stevens is Slate’s film critic and a co-host of Slate’s Culture Gabfest podcast, and a contributor to the Bookends column at the New York Times Book Review. Her Twitter handle is @thehighsign.

This ends our Movie Of The Week discussion of Lovely & Amazing. Don’t miss Tuesday’s Keynote on the art of conversation in Nicole Holofcener’s films, and Wednesday’s Forum on how the film tackles body image, perception of women, family connections, and more. Next week, join us for our discussion of Martin Scorsese’s squirmy dark humor in The King Of Comedy.