A Rainy Day in New York 2020

Gatsby Welles, the enigmatic offspring of New York City’s elite, navigates the hallowed halls of Yardley College in upstate New York as a bright but unconventional student. When his girlfriend, Ashleigh Enright (journalism major from Tucson), embarks on an investigative journey to Manhattan to interview esteemed independent filmmaker Roland Pollard for their college newspaper, Gatsby seizes the opportunity to join her, intent on conjuring a romantic getaway amidst the city’s iconic skyline. However, his parents’ meticulously planned gala that evening casts a shadow over their plans, as he struggles with his complicated relationship with them.

Ashleigh’s interview with Pollard is supposed to be a brief encounter, but the director’s invitation to a private screening of his latest film derails her plans with Gatsby, much to his dismay. As Ashleigh becomes increasingly entwined in Pollard’s creative crisis and his screenwriter, Ted Davidoff, Gatsby finds himself solo, wandering the city streets. A chance encounter with an old acquaintance, a film student shooting a short film, prompts him to fill in for a missing actor, leading to an unexpected kiss from none other than Chan Tyrell, the younger sister of a former flame.

The coincidence is not lost on Gatsby, whose plans are further derailed when he and Chan happen upon the same taxi. Feeling abandoned and without direction, Gatsby accompanies Chan to her parents’ apartment, where they bond over their shared love for New York City’s rain-soaked charm. A serenade of “Everything Happens to Me” on their piano sets the tone for a nostalgia-filled evening that culminates in a visit to the Metropolitan Museum of Art. It is there that Chan confesses her long-held crush on Gatsby, adding a layer of complexity to their blossoming connection. Meanwhile, an unexpected encounter with his aunt and uncle at the museum forces Gatsby to confront his responsibilities and attend his parents’ gala that evening.

As Ashleigh and Ted’s search for missing Pollard yields no results, they stumble upon an unexpected revelation - Ted’s wife is having an illicit affair. Meanwhile, Ted confronts his unfaithful spouse, while Ashleigh finds herself swept up in a world of glamour at the studio where she meets charming film star Francisco Vega (Francisco Vega), who invites her to join him for dinner. Amidst this chaos, Gatsby employs his exceptional poker skills to win big at a high-stakes game arranged by his brother earlier that evening. However, as he retreats to his hotel room, he’s met with the jarring news of Ashleigh being hailed as Francisco’s latest conquest on television.

Distraught and seeking solace, Gatsby heads to the Carlyle Hotel’s cocktail lounge, where he encounters Terry, a stunning escort who agrees to pose as the absent Ashleigh at his family’s gala. Back in the world of film, Francisco takes Ashleigh to an exclusive party, reuniting her with Pollard and Ted, both of whom declare their admiration for her. As the night wears on, Francisco and Ashleigh find themselves alone in his apartment, poised to take their relationship to the next level. However, the sudden arrival of Francisco’s girlfriend sends Ashleigh fleeing into the rain, clad only in a raincoat over her lingerie.

The following evening, Gatsby arrives at his family’s gala with Terry by his side, but his mother sees through the ruse. In a poignant conversation, she reveals to Gatsby that she was once an escort herself, using her earnings as seed capital for their family’s wealth. This surprising revelation changes Gatsby’s perception of his mother and her motivations behind pushing him towards intellectual and artistic pursuits. As the night draws to a close, Ashleigh finds a despondent Gatsby back at the Carlyle, assuring him that nothing transpired with Francisco, despite her compromised state.

The next morning, before departing Yardley, the couple takes a horse-drawn carriage ride through Central Park, but Ashleigh’s spirits are dampened by the misty weather. When Gatsby quotes a Cole Porter lyric, she mistakenly attributes it to Shakespeare, leading him to realize their incompatibility. Gatsby abruptly ends their relationship and announces his decision to withdraw from Yardley, opting instead to stay in New York. Later, he visits the Delacorte Clock outside the Central Park Zoo, reenacting a fantasy shared with Chan. As the clock strikes six, Chan arrives, and the pair share a passionate kiss in the pouring rain.