Skylar and Holden are an upper-class Manhattan couple navigating the social web of their circle, a relationship that begins with a grand gesture and quickly spirals into a tangle of loyalties, desires, and misread signals. Holden, hoping to cement his commitment, enlists Skylar’s younger sister, DJ, Joséphine, to help him choose an expensive diamond engagement ring. DJ’s influence and the couple’s expectations collide in a moment that sets off a chain of choices that ripple through the family and their friends. Skylar, who wants a partner who can seem to take charge, finds that her fantasies about romance clash with the messy reality of love.
On the other side of the scene, Steffi and Bob Dandridge are liberal Democratic lawyers who must balance their political passions with a blended family formed from previous marriages. They have a Republican son, Scott, who wants criminals off the streets and disapproves of Steffi’s work rehabilitating felons. Steffi brings to the engagement party one of her causes, Charles, a man who unsettles the room with stories of prison stabbings. Initially alarmed by Charles’s aggressive advances, Skylar finds herself drawn to him, and this attraction helps fracture her relationship with Holden. The dynamics between Steffi, Bob, and Joe—the neurotic ex-husband who lives in Paris—add a layer of bittersweet humor and tension as Steffi tries to fix Joe up with someone more suitable, even as Joe remains stuck on her.
Meanwhile, DJ heads to Venice, Italy with her father Joe, and the two listen in on therapy sessions through a wall, adding a voyeuristic thread to the narrative. There, Von, an art historian and one of the clients, confesses her own discontent with her husband and longs for romance. DJ urges Joe to “run into” Von and coaches him on how to woo her—faking shared interests in art, music, travel, and even a hastily assembled Parisian garret, plus a few coincidental meetings at a museum and a concert. Believing she has found the man of her dreams, Von leaves her husband for Joe, and the pair begin a romance that highlights the film’s playful, almost satirical tone toward modern love.
DJ’s romantic odyssey continues back in New York, as she falls for a gondolier and contemplates dropping out of college to marry him, only to meet another potential flame, a Columbia student, followed by a rapper in the city and finally a dashing Parisian. The sisters Lane and Laura—DJ’s half-siblings—also chase their own crushes around their social milieu, adding a lighter subplot about youth, ambition, and the search for belonging. The Vandermost heir adds a note of wealth and prestige to the mix, and Laura’s heartbreak when Vandermost chooses Lane layers in a touch of sibling rivalry to the ensemble.
The family’s humor and warmth are punctured by Grandpa, an 88-year-old with dementia who roams the house, managed by Freda the maid in a running joke that turns darker and more surreal as the funeral for Grandpa becomes a mix of comedy and memory. In a moment of theatrical whimsy, the chapel’s dead bodies sing and dance to “Enjoy Yourself (It’s Later than You Think).” Skylar’s entanglements grow riskier when she encourages ex-con Charles to study law, only to become involuntarily wrapped up in a getaway-gone-wrong with his gang in a grocery-store robbery. She begs to be released from the car, manages a narrow escape, and eventually reconciles with Holden at a Halloween Party, where the couple’s fragile bond is tested once more when Skylar swallows the engagement ring Holden had slipped into a box of Cracker Jack, a sequence that mirrors the film’s recurring motif of mislaid love and second chances.
Scott’s story offers a counterpoint of possible redemption when he is diagnosed with a brain tumor and undergoes surgery, after which he resigns from the Young Republicans Club and begins to espouse left-wing causes. Von’s arc also shifts; after her fling with Joe, she returns to her husband, leaving Joe to confront his own longing and the realities of their situation.
The family eventually travels to Paris for Christmas and rings in the New Year with a Groucho Marx–themed party, followed by a cold that brings Steffi back into contact with Joe. Their past marriage is acknowledged with an adult, nuanced tenderness: Steffi loves Bob “wholeheartedly,” and while she and Joe acknowledge lingering feelings, they choose to maintain boundaries that support each other’s happiness. The closing image finds the family dancing to a lively, retro soundtrack—DJ finally finding a dance partner in a Harpo Marx costume—while the story circles back to the idea that love, in its many forms, still has a way of finding everyone, even when it wears a mismatched glove.
Key moments weave together humor, romance, and a light sense of inevitability, presenting a portrait of a multi-generational, cosmopolitan clan where aspirations collide with the messy beauty of real life. The film’s tone remains warm and gently ironic, celebrating the joy and chaos of love, family, and the city that houses it all.
