A Rainy Day in New York

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 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.

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’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.

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’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 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.

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.

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 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.

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 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 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.

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.

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.