A Rainy Day in New York

The film unfolds across New York City's most iconic locations, including the Metropolitan Museum of Art, the Carlyle Hotel, and Central Park. These prestigious venues serve as the backdrop for the characters' romantic encounters and personal discoveries. The city's glamorous atmosphere and rainy weather become central to the film's mood.

The story is set in contemporary times, unfolding over a single rainy weekend in New York City. This modern setting blends current dating culture with a refined, cinematic romance. The rainy weather and urban interiors create moments of vulnerability and sudden connection between characters.

The rain acts as a catalyst for vulnerability, exposing the characters' hopes, insecurities, and longing for lasting connection. It transforms the city into a stage for emotional honesty, making love feel both exhilarating and elusive. The weather mirrors the characters' internal emotional states throughout the weekend.

The film explores three interconnected themes: romance under challenging circumstances, the glamorous yet fragile world of showbiz, and the impact of family secrets on personal identity. These themes weave together through the characters' interactions and choices over the weekend.

Gatsby Welles is a bright, witty, and impulsive student played by Timothée Chalamet. He possesses gambling savvy and navigates a weekend of romance while balancing parental expectations and his own ambitions. Restless and charming, he seeks a perfect New York moment that might redefine his future, ultimately pursuing emotional risk and self-discovery.

Ashleigh Enright is a journalism major from Tucson who travels to New York to interview a renowned director. Played by Elle Fanning, she is practical, keen-eyed, and determined, yet open to the magic of unexpected moments. Her interactions with Gatsby and other figures test both her professional resolve and romantic heart.

Their relationship evolves from playful flirtation into a deeper, more intimate connection as they navigate the rain-drenched streets together. The weekend in the city becomes a catalyst for vulnerability between them. Their bond represents the film's central exploration of romance as both exhilarating and elusive.

Early conversations between Gatsby and Ashleigh hint at their mutual curiosity about stepping outside their expected paths.

Through Ashleigh's interviews with directors and stars, the film reveals the blurred lines between art and spectacle. Ambition and charisma draw characters into glamorous events, while creative crises expose the fragility behind celebrity polish. This showbiz energy mirrors Gatsby's search for meaning beyond wealth and status.

Gatsby discovers that his mother has been funding the family wealth, a revelation that fundamentally reframes his understanding of success and parental influence. This disclosure prompts him to reevaluate his ambitions and consider the true cost of prestige. The secret ultimately shapes his sense of identity and the choices he makes going forward.

Earlier scenes featuring his mother hint at a level of sophistication and resources that exceed what a typical family wealth might suggest.

Chan Tyrell is a film co-star played by Selena Gomez, who is also the sister of Gatsby's former girlfriend. She brings a magnetic, independent presence to the story and sparks a complicated romance with Gatsby. Her choices reveal a longing for authenticity in a glittering world of fame.

Francisco Vega is a film star played by Diego Luna who befriends Ashleigh during her New York weekend. He embodies confident charm and a penchant for drama, inviting her to dinner and becoming a catalyst for the night's romantic entanglements. His interactions underscore the pull between art, romance, and ambition.

Ted Davidoff is a screenwriter played by Jude Law who is experiencing a creative crisis. His wife's affair becomes a backdrop to the professional world Ashleigh navigates during her interviews. He moves through the story offering a grounded, often anxious perspective on romance and art.

The film carries a whimsical tone characteristic of Woody Allen's signature dialogue and romanticized view of New York City. Chance encounters and clever wordplay drive the narrative forward. While it deals with themes of infidelity and incompatibility, the approach remains witty and observational rather than heavy or tragic.

The ending carries a bittersweet tone, the protagonist finds a new romantic connection but must end his existing relationship. Despite dealing with disappointment and relational conflict, the emotional weight remains light. The film balances romantic entanglements with observational humor, creating a nuanced yet accessible viewing experience.