Nicole Holofcener’s new film dissects the concentric circles of guilt and unhappiness that envelope two modern Manhattan families. One the one side we have Kate, played by the director’s muse Catherine Keener (this is their fourth collaboration). She and her husband Alex buy furniture from the clueless families of recently deceased old folks and then mark up and resell the antiques at their trendy store. Alex cheerfully dismisses this as business as usual; Kate is ruthless in the moment of opportunity but otherwise wears a pained and sour expression. She combats her rising feelings of guilt by giving money to homeless people on the street, much to the chagrin of her angsty daughter Abby. The quintessential teenager, Abby nags her mom for designer jeans and picks at her acne. The tension hangs between them like modern art on their walls, the prickly trappings of their forced lifestyle.

On the other side – next door – lives Andra, a caustic old woman who is looked after by her granddaughter Rebecca. A doe-eyed radiation technician, Rebecca spends her days giving women mammograms and her evenings caring for her grandmother. Occasionally her bitchy sister Mary sashays through to yell at Andra and make fun of Rebecca’s devotion. Amanda Peet does a nice turn as Mary; though cruel, and herself laughable as an overly tan facialist, she is often the only one who speaks the truth in this film.

The class differences that separate the two families are exacerbated by the fact that Kate and Alex have bought Andra’s apartment and are (somewhat guiltily) waiting for her to die so they can renovate and enlarge their own apartment. In a cringe-worthy scene the family has Andra and her granddaughters over for dinner. Mary swills too much bourbon and has Kate walk her through the imagined renovations, speaking of Andra’s death in front of her as though she were already gone. Kate resists, at first, but when pushed reveals her guilty enthusiasm for the project. This encapsulates Kate perfectly; she may allow herself to wallow in narcissistic guilt but ultimately pursues what she wants at the expense of others. She makes flaccid attempts to correct this flaw, giving money away and attempting to volunteer, but her perception of the world throws her off; she insults a Black man by offering him her leftovers, and finds her volunteer work so sad it reduces her to tears. Pitying those around her distracts her from the coldness of her own life, from her disintegrating family and unfulfilling work.

The two families become increasingly entangled as the film winds to a subtle climax. In the end there are small moments of hope and connection but they retain a taste of bitterness. A crowd-pleaser? No. But I like the edge in Holofcener’s work. I recently learned that her stepfather was a long-time Woody Allen collaborator and that Nicole spent time on his sets growing up. It’s a tenuous link but definitely visible in her deadpan, cynical humor. She twists and twists, giving little signs of the comfort to be gleaned from relationships of any kind (family, romantic, professional). Sadness thrums beneath this cold facade and breaks through in poignant moments. I count her earlier film Lovely & Amazing as one of my favorites; the scene where a neurotic actress has her lover list her flaws while standing naked before him is classic. Such astonishing directness is on display in Please Give as well but there’s less pathos to these characters. New York plays an important, decidedly unglamorous role, the city seeming to push people together not out of connection but out of need. But this isn’t Allen’s sun-dappled Upper East Side; Kate’s moral grappling with her wealth may be disingenuous but that’s exactly the point.