Here’s a quick reminder of the story of the classic Jewish 1988 film...
Crossing Delancey follows Isabelle Grossman (Amy Irving) a smart, bookish woman working at a Manhattan bookshop, drifting through a life that looks cultured and “sorted” from the outside and oddly unrooted from the inside. Her bubbe, played by Reizl Bozyk, wants her settled, loved, and less alone, and she takes matters into her own hands via a traditional matchmaker, arranging a meeting with Sam Posner, a warm, straightforward man who runs a pickle business and still belongs to the old neighbourhood life. Isabelle, played by Amy Irving, is intrigued by a different kind of man entirely: Anton Maes, a charming, married author who represents the glamorous, self-mythologising world she thinks she wants. Peter Riegert plays Sam as patient and quietly confident, someone who feels “real” in a way Isabelle keeps resisting until the film’s final turn pushes her to choose him.
The film was written by Susan Sandler, directed by Joan Micklin Silver of Hester Street fame and features delightful turns by Sylvia Miles as the shadchan and Yiddish theatre doyenne, Reizl Bozyk.
Part I: Dan’s view
I get why people remember this film fondly. The neighbourhood texture is vivid. The aunties, the food, the cadence of older Jewish New York, the sense of a world that’s half-vanished. The matchmaker isn’t a quirky gimmick; she’s a living remnant. And Bubbe, especially, is magnetic. She has that hard-soft mix a mythical Bubbe carries: practical, affectionate, meddling, lonely, funny. When she engineers the meeting, you can feel the love underneath the manipulation. She’s trying to hand her granddaughter a life that won’t fall into cleverness and isolation.
But the central romance, for me, asks for goodwill it hasn’t earned.
Isabelle’s behaviour towards Sam is consistently unflattering. She’s dismissive, then evasive, then oddly transactional.
She’s rude in the way someone can be rude when they think they’re being “honest”. She lets him feel the class line between them, even while pretending it’s just taste. Pickles, Delancey, old-world manners, the whole thing embarrasses her because it reflects her back to herself.
Sam pursues her anyway, despite barely knowing her. He watches her around the neighbourhood, builds a longing out of glimpses, and decides she’s the one. That can be romantic in the right story. Here it plays more like a stubborn projection. When he sends her the hat, it’s meant to read as sweet. It partly is. But it also gives Isabelle the chance to do something simple and decent: return it, or draw a clear line. She doesn’t. She accepts the gift and worse, she starts treating Sam as a prop in her own confusion. She goes to thank him and ends up implying interest she hasn’t felt. Then she arranges to introduce him to her friend without being straight with him about what she’s doing. It’s matchmaking by ambush, a mirror of what she resents from her Bubbe, but now she’s the one pulling the strings. She asks her friend if it’s OK, but the whole thing still has that sour flavour: “Here, you deal with him.” And then, when the friend responds positively, Isabelle’s interest flickers into life. That shift reads to me as status, ego, and competition, not love. He becomes valuable because another woman sees value in him. Isabelle is drawn to Anton because he flatters her self-image. Bookish. refined. worldly. A man who makes her feel like the kind of woman she imagines herself to be. The fact he’s married should be a moral line; in the film, it becomes part of the allure. It feels adolescent to me. When she finally sees Anton clearly, the revelation is that he wants a muse, not a partner.
He wants the feeling of her, not the responsibility of her. Fine. That’s a real disappointment. But the pivot back to Sam feels like he’s the backup plan, not a genuine love interest.
She runs back, and he’s there, waiting, basically ready to restart the story with no real cost. No sense that she understands what she did to him, or to her friend. Just a closing warmth that assumes the audience will supply the missing pieces.
I don’t see why Sam wants Isabelle beyond the surface. He likes how she looks and what she represents, then endures a long stretch of bad treatment because the story needs him to be the good option waiting at the end. Isabelle, meanwhile, doesn’t show enough generosity, honesty, or maturity to make the final pairing feel earned. The film wants the romance to be a homecoming.
To me it plays as a retreat: Anton fails her, so she takes the decent man who has remained available. If there’s romance here, it’s Bubbe’s romance. Her stubborn belief that love can be arranged, nudged, cooked into existence the way you get a brisket right. Her fear of her granddaughter ending up alone. Her longing for continuity. That’s the beating heart of the film. Isabelle and Sam feel like the vehicle.
Part II: Viola’s view
If there was one word to describe Sam, the romantic hero of Crossing Delancey, it could be summed up as follows: “schmuck.” Uttered by the man himself, after his date Izzy has messed him around yet again (having done so for pretty much the entire film). In many ways he’s not wrong. But to me, he’s never pathetic. Crossing Delancey is just about the sweetest, most romantic film there is. Firstly there’s something effortlessly magical about Eighties rom-coms set in New York that just nail the genre so perfectly. Plus there’s a bossy Jewish grandma. And a lady singing Some Enchanted Evening while people are eating hot dogs. What’s not to like?
While most Jewish stories are about love across cultural and religious divides and breaking from tradition (see: Fiddler on the Roof, Nobody Wants This), Crossing Delancey is one of the few films to extol the virtues of marrying in, of reclaiming and reconnecting to one’s heritage and the beauty of keeping certain traditions alive. And having myself grown up extremely assimilated with little knowledge of my roots, part of me could sympathise with Izzy’s plight (not to condone her behaviour).
Her hot and cold behaviour towards Sam isn’t solely about her being fickle and thoughtless (although she is), it’s her conflicted attitude towards her own culture, represented by Sam (who sells pickles, fishing them out of the barrel with his bare hands); her meddling bubbe; the nosy (and very noisy) matchmaker Mrs Mendelbaum and the rough-and-ready world of the Lower-East Side these characters inhabit. It’s a stark contrast to the bougie Manhattan literary scene Izzy frequents. She flits between two worlds and compartmentalises them in her mind, although she is deeply fond of her bubbe and cares for her (which arguably makes us more forgiving of her treatment of Sam).
She’s in various situationships. There’s Anton Maes – a douchebag author at the bookstore she works at (in one cringey scene, he recites a poem about “ripe plums” while staring deeply into her eyes – ew!). As well there’s Nick – a bearded schlub who turns up at her apartment like a stray cat whenever his wife kicks him out. So Bubbe decides to take matters into her own hands, hiring Mrs Mendelbaum to find Izzy a shidduch. Enter Sam, who by contrast to the other men, is sweet and kind, and pursues Izzy earnestly and relentlessly, willing to make a fool of himself, despite her initial snooty reluctance. (“This isn’t the way I live.”) But with Bubbe’s encouragement Sam gently persists. Bubbe is like a fairy godmother, albeit a brash, Yiddishe version with chin hairs and arthritis. Izzy ums and ahs, flouncing around in the brown hat he buys her even after she says she’s not interested, sets him up with one of her friends then immediately gets jealous. At one point he understandably gets tired of her nonsense, but Grandma intervenes and lures him back in encouraging him to just hang on in there.
During the final scene, where Izzy arrives at Bubbe’s apartment (where she had arranged to meet Sam for dinner several hours earlier) she collapses into tears thinking she has lost him for ever because of her stupidity and self-sabotage. Only to discover he’s just… still there. (I always breathe a sigh of relief at this bit, despite having seen this film about 200 times.) She might not have deserved another chance, but we all know – as she does – that he’s actually going to be good for her. To me, that’s the romantic message of Crossing Delancey: love isn’t about some pretentious author reading you poetry, it’s a pickle man who still shows up when you’re being an idiot. Bubbe knows best after all.
Coda
Having discussed their respective written submissions, Dan and Viola agree on one thing: to never buy pickles from a guy who uses his hands to fish them out.
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