A Rainy Day in New York

A Rainy Day in New York

Year: 2019

Runtime: 92 mins

Language: English

Director: Woody Allen

Echo Score: 65
ComedyRomance

Two young people arrive in New York to spend a weekend, but once they arrive they’re met with bad weather and a series of adventures.

A Rainy Day in New York (2019) – Spoiler-Free Movie Summary & Plot Overview

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In a city that never quite lets the clouds clear, Gatsby Welles arrives with a restless mind and a pocketful of good‑fortune, hoping a weekend in Manhattan will be the perfect backdrop for a romance and a break from the expectations of his affluent family. Beside him, Ashleigh Enright steps off the train from Tucson, notebook in hand, eager to interview the celebrated independent filmmaker Roland Pollard for her college newspaper and to soak up the electric buzz of the city that has long existed only in her imagination.

Both carry their own ambitions: Gatsby, a gifted gambler and a student at an upstate liberal‑arts college, is determined to sidestep a looming gala that represents his parents’ world of polish and propriety; Ashleigh, a journalism major with a keen eye for stories, hopes the interview will launch her career while also giving the pair a chance to explore the streets together. The forecast, however, drifts toward relentless rain, turning the city’s iconic skyline into a shimmering veil that mirrors the couple’s uncertain emotional weather.

Against the backdrop of drizzle‑slicked sidewalks, towering museums, and the perpetual hum of taxis, the weekend unfolds as a series of serendipitous encounters that pull Gatsby and Ashleigh into the orbit of eccentric artists, restless students, and strangers whose lives intersect with the city’s endless narratives. The rain becomes a character of its own—softening the harsh angles of Manhattan while amplifying its romantic, almost cinematic quality. As the two navigate galleries, cafés, and dimly lit lounges, the line between planned itinerary and spontaneous adventure blurs, promising a weekend that will test their expectations and reveal new facets of love, ambition, and the unmistakable magic that only a rainy day in New York can conjure.

Last Updated: November 25, 2025 at 14:46

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Serendipitous love stories unfolding against the backdrop of a vibrant city.Discover movies like A Rainy Day in New York that feature charming, serendipitous love stories set against the backdrop of a bustling metropolis. If you liked the romantic, city-centric vibe of this film, you'll enjoy these other stories where the urban landscape plays a key role in the narrative.

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Narrative Summary

The narrative follows protagonists as they navigate a romantic entanglement that exposes fundamental incompatibilities or personal flaws. The conflict is primarily internal and relational, leading to a conclusion that is realistically bittersweet—often involving a breakup or a shift in perspective—but ultimately focused on personal growth rather than tragic loss.

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They are united by a moderate complexity in exploring relationship dynamics, a bittersweet ending feel, and a light-to-medium emotional weight that treats the subject with witty observation rather than heavy tragedy. The tone balances romantic hope with pragmatic realization.

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A Rainy Day in New York Summary

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Characters, Settings & Themes in A Rainy Day in New York

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