Gatsby Welles, the brainy but eccentric son of wealthy New York City-based parents, is a student at Yardley College, a liberal arts school in Upstate New York, and a successful gambler. When his girlfriend Ashleigh Enright, a journalism major from Tucson, has to travel to Manhattan to interview esteemed independent filmmaker Roland Pollard for the student newspaper, Gatsby tags along, planning a romantic weekend in the city, while trying to avoid his parents who are holding 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 he is impressed by her charm and film knowledge and 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 is shooting a short film and asks him to stand in for a missing actor for a shot which involves kissing his co-star. To Gatsby’s surprise, the actress turns out to be Chan Tyrell, the younger sister of a former girlfriend. The two of them run into each other again when they both hail the same cab. Gatsby’s romantic plans with Ashleigh are further delayed by Ashleigh getting increasingly involved with both Pollard, who is having a creative crisis, and his long-suffering screenwriter Ted Davidoff.
Feeling abandoned, Gatsby joins Chan to her parents’ apartment and sings “Everything Happens to Me” on their piano. They discuss their love for New York and agree it is one of the most romantic places on rainy days, then go to the Metropolitan Museum of Art, where she admits she used to have a crush on him. A chance meeting with his aunt and uncle at the museum forces him to attend his parents’ gala.
While chasing after a disappeared Pollard, Ashleigh and Ted stumble upon Ted’s wife, who is having an affair. While Ted confronts his wife, Ashleigh goes to the studio where she meets film star Francisco Vega, who invites her out for drinks. Gatsby, meanwhile, uses his gambling skills to win big at a poker game his brother had procured earlier in the evening. Back at his hotel room, he sees Ashleigh on the news hailed as Francisco’s latest fling. Distraught, he goes for a drink at the Carlyle’s cocktail bar, where he meets an escort named Terry, whom he decides to hire 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 go back to his apartment. As they start to make out, his out-of-town girlfriend arrives unexpectedly, driving Ashleigh to leave through the backdoor wearing only a raincoat over her bra and panties.
Gatsby arrives at his family’s gala with Terry, but his mother quickly sees through the charade. She sits down with Gatsby and reveals that she herself was an escort when she met his father, and her own savings are what gave him the starting capital that resulted in their wealth, which is the reason why she kept pressuring Gatsby into all kinds of intellectual and artistic endeavors, the education and refinement she had to acquire only as an adult. This revelation entirely changes Gatsby’s opinion on his mother. At the end of the night, Ashleigh finds a despondent Gatsby back at the Carlyle, assuring him that nothing happened with Francisco.
The next morning, Ashleigh recounts to Gatsby all about her emotional and sexual misadventures of the previous day. They decide to take a horse-drawn carriage ride in Central Park before returning to Yardley. 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 decides to stay in New York. He later goes to the Delacorte Clock outside the Central Park Zoo, which was part of a fantasy he and Chan previously shared. When the clock strikes 6 p.m., Chan arrives, and they kiss under the pouring rain.