A Rainy Day in New York 2019
Directed by
Rebecca Hall
Made by
Gravier Productions
A Rainy Day in New York Plot Summary
Read the complete plot summary and ending explained for A Rainy Day in New York (2019). From turning points to emotional moments, uncover what really happened and why it matters.
Gatsby Welles, Timothée Chalamet, is the brainy but eccentric son of wealthy New York City–based parents and a student at Yardley College, a liberal arts school in upstate New York. He is also a skilled gambler. When his girlfriend, Ashleigh Enright, Elle Fanning, a journalism major from Tucson, must travel to Manhattan to interview the esteemed independent film director Roland Pollard Liev Schreiber for the student newspaper, Gatsby tags along, planning a romantic weekend in the city, while trying to avoid his parents who are hosting a gala in the evening, and with whom he has a conflicted relationship.
Ashleigh’s interview with Pollard is supposed to last one hour, but the director invites her to a private screening of his new film, which ruins her plans with Gatsby, much to his dismay. Strolling alone through New York, Gatsby bumps into a film student friend who asks him to stand in for a missing actor for a shot that involves kissing his co-star. To Gatsby’s surprise, the actress turns out to be Chan Tyrell, Selena Gomez, the younger sister of a former girlfriend. The two run into each other again when they hail the same cab. Gatsby’s romantic plans are further delayed by Ashleigh growing closer to Pollard, who is having a creative crisis, and his long-suffering screenwriter, Ted Davidoff Jude Law.
Feeling abandoned and adrift, Gatsby accompanies Chan to her parents’ apartment where he sings “Everything Happens to Me” on their piano. They discuss their love for New York and agree that, on rainy days, it is one of the most romantic places. They visit the Metropolitan Museum of Art, where Chan confesses that she once had a crush on Gatsby. A chance encounter with his aunt and uncle at the museum forces Gatsby to attend his parents’ gala later that evening.
Meanwhile, while searching for a vanished Pollard, Ashleigh and Ted stumble upon Ted’s wife, who is having an extramarital affair. While Ted confronts his wife, Ashleigh goes to the studio where she meets film star Francisco Vega Diego Luna, who invites her out for dinner. Gatsby, meanwhile, uses his gambling skills to win big at a poker game his brother had arranged earlier in the evening. Back at his hotel room, he sees Ashleigh on the television news hailed as Francisco’s latest fling. Distraught, he goes for a drink at the Carlyle Hotel’s cocktail lounge, where he meets an escort named Terry, whom he hires to impersonate Ashleigh at his family’s gala.
Francisco takes Ashleigh to a film business party, where she reconnects with Pollard and Ted, who both declare themselves smitten with her. Afterwards, Francisco and Ashleigh retire to his apartment, and as they are about to have sex, Francisco’s girlfriend arrives unexpectedly, driving Ashleigh to leave through the backdoor into the rain, wearing only a raincoat over her bra and panties.
Gatsby arrives at his family’s gala with Terry, but his mother sees through the charade. In an intimate talk, she reveals to Gatsby that she was an escort when she met his father, and that her earnings were the seed capital that resulted in their wealth. Her personal history is the reason she has pressured Gatsby into intellectual and artistic endeavors, education, and refinement that she acquired as an adult. This revelation changes Gatsby’s perceptions of his mother in a positive way. At the end of the night, Ashleigh finds a despondent Gatsby back at the Carlyle, assuring him that nothing happened with Francisco, despite her lack of clothing.
The next morning, before their planned return to Yardley, the pair take a horse-drawn carriage ride in Central Park. Ashleigh, however, is disappointed by the misty weather, and when Gatsby mentions a Cole Porter lyric, she misattributes it to Shakespeare. Realizing their incompatibility, Gatsby abruptly ends their relationship and announces that he will withdraw from Yardley to stay in New York. He later goes to the Delacorte Clock, outside the Central Park Zoo, reenacting a fantasy he and Chan previously shared. As the clock strikes six, Chan arrives, and the pair kiss in the pouring rain.
A Rainy Day in New York Timeline
Follow the complete movie timeline of A Rainy Day in New York (2019) with every major event in chronological order. Great for understanding complex plots and story progression.
Gatsby plans a NYC weekend as his gala looms
Gatsby Welles, a brilliant yet restless student and gambler from a wealthy New York family, plans a romantic weekend in New York with Ashleigh while trying to dodge his parents’ gala that evening. He wants to keep things carefree, even as his family celebrations loom in the evening. The setup introduces the pairing’s tension between intellect, romance, and high-society expectations.
Ashleigh travels to Manhattan for Pollard interview
Ashleigh Enright travels to Manhattan to interview director Roland Pollard for the student newspaper. Gatsby tags along, hoping for time with her in the big city. This trip begins the city-centered weekend that will pull their lives into Pollard’s orbit.
Gatsby substitutes for a missing actor; meets Chan Tyrell
A film student asks Gatsby to stand in for a missing actor in a kiss-shot, and the actress turns out to be Chan Tyrell, the younger sister of Gatsby’s ex-girlfriend. The encounter pulls them into a new, complicated dynamic. Their chemistry sets up a recurring connection that will complicate Gatsby’s plans with Ashleigh.
Pollard invites Ashleigh to a private screening
Pollard’s one-hour interview turns into a private screening that derails Ashleigh’s plans with Gatsby. The screening reveals Pollard’s creative crisis and pulls Ashleigh deeper into his circle. Gatsby watches the shift from the sidelines as plans unravel.
Cab encounter with Chan rekindles a spark
Gatsby and Chan run into each other again when they hail the same cab in the city lights. The coincidence fuses their growing attraction and hints at a more tangled love story beyond Ashleigh. This late-night meet feels fated within the New York romance going on around them.
Ashleigh draws closer to Pollard and Ted Davidoff
Ashleigh’s NYC weekend becomes entangled with Pollard’s artistic crisis and his screenwriter, Ted Davidoff. The professional and personal lines blur as Gatsby’s pursuit of her contends with Pollard and Ted’s influence. The triangle deepens the narrative’s romantic tension.
Gatsby and Chan visit Chan’s parents; piano serenade
Gatsby accompanies Chan to her parents’ apartment, where he plays 'Everything Happens to Me' on the piano. They discuss their shared love for New York and agree that rainy days can feel especially romantic. The moment solidifies their bond amid the surrounding city chaos.
Museum date; Chan’s crush and gala pressure
The couple visits the Metropolitan Museum of Art, where Chan confesses a past crush on Gatsby. A chance encounter with Gatsby’s aunt and uncle at the museum pushes him toward his parents’ gala later that evening. The museum visit blends romance with social obligations and family expectations.
Ashleigh and Ted uncover an affair; Francisco invites dinner
While searching for Pollard, Ashleigh and Ted stumble upon Ted’s wife having an extramarital affair. Ted confronts his wife, and Ashleigh goes to a studio where she meets film star Francisco Vega, who invites her to dinner. The discoveries heighten the film’s romantic and professional tensions.
Gatsby’s poker win and Ashleigh’s TV rumor
Gatsby uses his gambling skills to win a big poker game arranged by his brother. Back at his hotel room, he sees Ashleigh on television hailed as Francisco Vega’s latest fling. Distraught, he heads to the Carlyle Hotel to drink and regroup.
Gatsby hires Terry to impersonate Ashleigh
In a desperate bid to salvage the gala, Gatsby hires escort Terry to impersonate Ashleigh at his family gathering. The ruse exposes Gatsby’s fragility and the performative glamour of their social circle. The deception strains his relationship with his mother and Ashleigh.
Francisco party; Ashleigh departs in the rain
Francisco takes Ashleigh to a film industry party where she reconnects with Pollard and Ted, who both express their interest. Francisco’s girlfriend arrives unexpectedly, forcing Ashleigh to slip out through the back door into the rain. The night exposes dangerous romantic overlaps.
Gatsby’s gala reveal; mother’s past comes to light
Gatsby arrives at his family’s gala with Terry, and his mother reveals she was an escort whose earnings seeded the family fortune. The confession reframes Gatsby’s view of his mother and clarifies the pressure he feels to be refined and educated. The moment adds warmth and complexity to their bond.
Central Park morning carriage; decision to stay
The next morning, Gatsby and Ashleigh take a horse-drawn carriage ride through Central Park after a misty night. A misattributed Cole Porter lyric underscores their misalignment, and Gatsby announces he will withdraw from Yardley to stay in New York. The couple faces an uncertain future.
Rainy Delacorte kiss; Chan reunion
Gatsby goes to the Delacorte Clock in Central Park to reenact a shared fantasy with Chan. As the clock strikes six, Chan arrives and they kiss in the pouring rain, ending the film on a romantically hopeful note amid the city rain.
A Rainy Day in New York Characters
Explore all characters from A Rainy Day in New York (2019). Get detailed profiles with their roles, arcs, and key relationships explained.
Gatsby Welles (Timothée Chalamet)
A bright, witty, and impulsive student with gambling savvy, navigating a weekend of romance while balancing parental expectations and his own ambitions. He is charming and restless, seeking a perfect NYC moment that might redefine his future. His quick humor and restless curiosity drive him toward emotional risk and self-discovery.
Ashleigh Enright (Elle Fanning)
A journalism major from Tucson who travels to interview a renowned director, torn between professional commitments and romantic possibilities. She is practical, keen-eyed, and determined, yet open to the magic of a New York moment. Her interactions with Gatsby and Pollard test her resolve and heart.
Chan Tyrell (Selena Gomez)
A film co-star and sister to a former girlfriend, Chan moves through the story as a magnetic, independent presence who sparks a complicated romance with Gatsby. She embodies a blend of professional poise and vulnerable curiosity, navigating fame and personal connection. Her choices reveal a longing for authenticity in a glittering world.
Francisco Vega (Diego Luna)
A film star who befriends Ashleigh, inviting her to dinner and becoming a catalyst for the night’s romantic entanglements. He embodies confident charm and a penchant for drama, complicating Ashleigh’s weekend plans. His interactions underscore the pull between art, romance, and ambition.
Ted Davidoff (Jude Law)
A screenwriter experiencing a creative crisis, whose wife's affair becomes a backdrop to Ashleigh and Pollard’s professional world. He moves through the story with a mix of wit and inner conflict, offering a grounded, often anxious perspective on romance and art. His arc intersects with themes of trust and fidelity.
Mrs. Welles (Cherry Jones)
Gatsby’s mother, a poised matriarch who reveals a pivotal truth about the family’s wealth and past, reframing Gatsby’s understanding of his upbringing. Her openness about long-hidden choices reshapes his worldview and aspirations. She embodies sophistication, influence, and a willingness to confront difficult truths.
Aunt Grace (Mary Boyer)
A supportive family presence who attends the gala, offering warmth and stability within the social whirl. Her calm, nurturing demeanor contrasts with the night’s glitter and drama, anchoring Gatsby’s sense of family history. She represents enduring support in a world of spectacle.
Uncle Tyler (Ted Neustadt)
A traditional, steady uncle figure who participates in the gala world without losing his grounded perspective. He provides a cultural anchor amid the city’s glamour and family dynamics, helping to balance the evolving story. His presence reinforces themes of lineage and expectation.
A Rainy Day in New York Settings
Learn where and when A Rainy Day in New York (2019) takes place. Explore the film’s settings, era, and how they shape the narrative.
Time period
Set in contemporary times, the events unfold over a rainy weekend in New York City. The mood blends modern dating with a refined, cinematic romance. The weather and urban interiors heighten moments of vulnerability, doubt, and sudden connection.
Location
New York City, Central Park, Metropolitan Museum of Art, Carlyle Hotel, Delacorte Clock
New York City is the film’s busy, atmospheric backdrop, with scenes moving between museums, luxury hotels, and famous parks. The Metropolitan Museum of Art and the Carlyle Hotel anchor the city’s cultured glamour, while Central Park provides a rain-soaked stage for chance encounters. The city’s iconic venues and energetic mood shape the mood of desire, art, and ambition.
A Rainy Day in New York Themes
Discover the main themes in A Rainy Day in New York (2019). Analyze the deeper meanings, emotional layers, and social commentary behind the film.
🌧️
Romance
Gatsby and Ashleigh's weekend in the city evolves from playful flirtation into a deeper, more intimate connection under rain-drenched streets. The rain becomes a catalyst for vulnerability, exposing hopes, insecurities, and the longing for something lasting. The film uses the NYC weather and venues to frame love as both exhilarating and elusive.
🎬
Showbiz
Ashleigh’s interviews and encounters with directors and stars reveal the blurred lines between art and spectacle. Ambition and charisma draw characters into glamorous events, while creative crises expose the fragility behind celebrity polish. The film’s film-world energy mirrors Gatsby’s search for meaning beyond wealth.
💡
Family Secrets
A revelation about Gatsby’s mother funding the family wealth reframes his view of success and parental influence. The disclosure prompts him to reevaluate his ambitions and the true cost of prestige. The secret shapes his sense of identity and the choices he makes going forward.
A Rainy Day in New York Spoiler-Free Summary
Discover the spoiler-free summary of A Rainy Day in New York (2019). Get a concise overview without any spoilers.
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.
Movies with Similar Twists and Themes
Uncover films that echo the narrative beats, emotional arcs, or dramatic twists of the one you're exploring. These recommendations are handpicked based on story depth, thematic resonance, and spoiler-worthy moments — perfect for fans who crave more of the same intrigue.
Featured on this page
What's After the Movie?
Not sure whether to stay after the credits? Find out!
Explore Our Movie Platform
New Movie Releases (2025)
Famous Movie Actors
Top Film Production Studios
Movie Plot Summaries & Endings
Major Movie Awards & Winners
Best Concert Films & Music Documentaries
Movie Collections and Curated Lists
© 2025 What's After the Movie. All rights reserved.