The movie’s basic premise—two college sweethearts go to New York to spend a weekend together only to get themselves separated and embroiled in a series of misadventures—may not sound especially ambitious but it is one that could theoretically be spun out into a pleasant diversion in the hands of a writer as gifted as Allen. Unfortunately, once the opening credits, scored to Bing Crosby crooning “I Got Lucky in the Rain,” have concluded, the whole enterprise goes off the rails right then and there with the introduction of the central male character, a brilliant but directionless bon vivant college student. His name, I kid you not, is Gatsby Welles, which has to be the most ridiculous moniker in the Allen oeuvre since Fielding Mellish. This is bad enough but the pain is compounded by the awkward and charmless performance by Timothée Chalamet as Gatsby. Like so many lead actors in the Allen films where he doesn’t appear, he gives a performance where he has been clearly asked to deliver his lines in as close of an approximation to Allen’s familiar cadences as he can muster.
The plot is launched into motion when Gatsby’s girlfriend, intrepid-but-ditsy student journalist Ashleigh Enright (Elle Fanning), snags an interview for the school paper with famous filmmaker Roland Pollard (Liev Schreiber) and he has the idea of making a fancy weekend of it funded by his recent poker winnings—drinks at the Carlyle, museum trips and, most importantly, avoiding a big party being thrown by his socialite mother (Cherry Jones). Things go south after they arrive when Ashleigh goes off to her interview and finds Roland in an existential and creative funk and contemplating giving it all up. He brings Ashleigh to a private screening of his new film but is so appalled with the movie that he bolts to go off on a bender, leaving his longtime collaborator, Ted Davidoff (Jude Law) to try to track him down, of course bringing Ashleigh along since she actually loves the film. This leads to her encountering a famous actor (Diego Luna) as well and before long, all three men find themselves besotted with her beauty, her unspoiled innocence, and her inability to hold her liquor.
With time on his hands, Gatsby wanders around, visits his brother Hunter (Will Rogers), who is contemplating cancelling his impending marriage because he is put off by the sound of his fiancee’s laughter, and eventually winds up being pressed into service for a friend directing a student film who needs someone for a scene in which they passionately kiss the lead actress. This is Chan (Selena Gomez), who happens to be the younger sister of one of Gatsby’s old girlfriends, and who may have had a crush on him herself. The two wind up spending much of the afternoon together before he is eventually dragooned into appearing at his mother’s party. With Ashleigh still MIA, he ends up hiring a sex worker (Kelly Rohrbach) to pose as her, a move that winds up having unexpected repercussions to his relationship with his mom.