Gatsby Welles, the mysterious scion of New York City's upper crust, navigates the prestigious Yardley College in upstate New York as a bright yet unconventional student. When his girlfriend, Ashleigh Enright, a journalism major from Tucson, sets off on an investigative mission to Manhattan to interview the revered independent filmmaker Roland Pollard for their college newspaper, Gatsby eagerly seizes the chance to accompany her, hoping to craft a romantic escapade against the backdrop of the city's iconic skyline. However, the evening's gala meticulously planned by his parents casts a cloud over their intentions, forcing Gatsby to grapple with his complex relationship with them.
What was meant to be a brief interview quickly spirals into a deeper engagement as Pollard invites Ashleigh to a private screening of his latest film, leaving Gatsby feeling sidelined and disappointed. As Ashleigh immerses herself in Pollard's artistic turmoil alongside screenwriter Ted Davidoff, Gatsby finds himself wandering the vibrant streets of New York alone. A fortuitous meeting with an old acquaintance, an aspiring filmmaker shooting a short film, leads him to step in for a missing actor, resulting in an unexpected kiss from Chan Tyrell, the younger sister of a past love.
This twist of fate is not lost on Gatsby, especially when he and Chan coincidentally share the same taxi. Feeling adrift and abandoned, Gatsby accompanies Chan to her parents' apartment, where they forge a connection over their mutual appreciation for New York City's rainy allure. An impromptu rendition of "Everything Happens to Me" on the piano highlights a night filled with nostalgia and culminates in a visit to the Metropolitan Museum of Art, where Chan confesses her long-standing affection for him, complicating their burgeoning relationship. Amid these developments, an unexpected reunion with his aunt and uncle at the museum compels Gatsby to face his obligations and attend the gala later that evening.
Meanwhile, Ashleigh and Ted's quest to locate Pollard leads to startling discoveries, including the revelation of Ted's wife's affair. As tensions rise, Ted confronts his unfaithful partner while Ashleigh finds herself indulged in glamour at a studio party, where she meets the charming film star Francisco Vega who invites her out for dinner. Amidst this whirlwind, Gatsby uses his adept poker skills to win a high-stakes game orchestrated by his brother. Yet, upon retreating to his hotel, he is blindsided by news of Ashleigh's depiction as Francisco's latest romantic interest on television.
Overwhelmed with distress, Gatsby seeks refuge in the Carlyle Hotel's cocktail lounge, where he meets the captivating escort Terry, who agrees to impersonate the absent Ashleigh at his family’s gala. In the film world, Francisco and Ashleigh reunite at an exclusive party, where both Pollard and Ted express their fondness for her. As the evening progresses, Francisco leads Ashleigh back to his apartment, where just as their relationship seems poised to become intimate, the unexpected arrival of Francisco's girlfriend sends Ashleigh fleeing into the rain, clad only in a raincoat over her lingerie.
The following night, Gatsby makes his appearance at the family gala with Terry, but his mother sees through his charade. In a heart-wrenching exchange, she reveals to Gatsby her past as an escort who used her earnings to build their family's fortune. This revelation transforms Gatsby's understanding of his mother, shedding light on her aspirations for him to engage in art and intellect. As the gala draws to a close, Ashleigh finds Gatsby despondent at the Carlyle, assuring him that nothing transpired between her and Francisco, despite her current state.
The next morning, as they prepare to leave Yardley, the couple enjoys a horse-drawn carriage ride through Central Park, although Ashleigh's mood is dampened by the misty weather. Gatsby quotes a lyric from Cole Porter, but Ashleigh mistakenly attributes it to Shakespeare, prompting Gatsby to realize their growing incompatibility. In a decisive moment, Gatsby ends their relationship and announces his intention to withdraw from Yardley, opting instead to remain in New York. Later, as he visits the Delacorte Clock outside the Central Park Zoo, he recalls a fantasy with Chan. When the clock strikes six, Chan arrives, and they share a passionate kiss amid the pouring rain, sealing their unexpected connection.
