In 2011, Gil Pender, a successful but creatively unfulfilled Hollywood screenwriter, and his fiancée Inez, are in Paris vacationing with Inez’s wealthy, conservative parents. Gil is struggling to finish his first novel, centered on a man who works in a nostalgia shop. Inez dismisses his ambition as a romantic daydream, and encourages him to stick with lucrative screenwriting. Gil is considering moving to Paris (which he notes, much to the dismay of his fiancée, is at its most beautiful in the rain). Inez is intent on living in Malibu. By chance, they are joined by Inez’s friend Paul, who is described as both pedantic and a pseudo-intellectual, and his wife Carol. Paul speaks with great authority but questionable accuracy on the highlights of Paris up to the point of even contradicting a tour guide at the Musée Rodin, and insisting that his knowledge of Rodin’s relationships is more accurate than that of the guide. Inez admires him; Gil finds him insufferable.
A night of wine tasting gets Gil drunk and he decides to walk the streets of Paris to get back to the hotel; Inez goes off with Paul and Carol by taxi. He stops to reconnoiter his location. At midnight, a 1920s car pulls up beside him, and the passengers, dressed in 1920s wardrobe, urge him to join them. They hit a party for Jean Cocteau attended by notable people of 1920s Paris: Cole Porter and his wife Linda Lee Porter, Zelda, and Scott Fitzgerald. Zelda gets bored at the party and encourages Scott and Gil to leave with her. They head first to Bricktops where they see Josephine Baker dancing, and then to a cafe, where they run into Ernest Hemingway and Juan Belmonte. Zelda gets upset when Hemingway says her novel was weak, and she heads with Belmonte to St. Germain, followed shortly thereafter by Scott, who doesn’t like the thought of his wife and the toreador. After discussing writing, Hemingway offers to show Gil’s novel to Gertrude Stein. As Gil exits the building to fetch his manuscript from his hotel, he finds he has returned to 2011; the bar where the 1920s literati were drinking is now a laundromat.
The next night, Gil wants to share with Inez his time travel experience. She ditches Gil before the clock strikes midnight. Before long, the same car returns; Gil joins Hemingway on his way to visit a friend. Gil is introduced to Gertrude Stein and other friends at her apartment: Pablo Picasso and his lover Adriana. Adriana and Gil are instantly attracted to each other. Stein reads aloud the novel’s first line:
‘Out of the Past’ was the name of the store, and its products consisted of memories: what was prosaic and even vulgar to one generation had been transmuted by the mere passing of years to a status at once magical and also camp.
Adriana says that she is hooked by these few lines and has always had a longing for the past, especially the Belle Époque.
Gil continues with his time travel for the next couple nights. Inez is annoyed at the boulevards and bistros and Gil’s wanderings. Her father is suspicious and hires a private detective to follow him. Adriana has her time with Picasso and Hemingway, and eventually Gil, although he is conflicted by his attraction to her. Gil confides his predicament to Salvador Dalí, Man Ray, and Luis Buñuel, but being surrealists they see nothing strange about his claim to have come from the future, finding it to be perfectly normal.
Each discusses the impossibility of Gil’s relationship with Adriana, and as artists, what work of art from each could come of the romance. Gil would suggest a film plot to Buñuel that is the cause of him attempting to understand the purpose of the plot.
Inez and her parents are traveling to Mont Saint Michel while Gil meets Gabrielle, an antique dealer and fellow admirer of the Lost Generation. He buys a Cole Porter gramophone record from her, and later finds Adriana’s diary from the 1920s at a book stall by the Seine, which reveals that she was in love with him. Reading that she dreamed of receiving a gift of earrings from him and then making love to him, Gil attempts to take a pair of Inez’s earrings to give to Adriana, but is thwarted by Inez’s early return to the hotel room.
Gil buys earrings for Adriana. Returning to the past, he finds her at a party and tells her, “I sense there are some complicated feelings you have for me.” He takes her for a walk, they kiss, and he gives her the earrings. While she’s putting them on, a horse-drawn carriage comes down the street, and a richly dressed couple inside the carriage invite Gil and Adriana for a ride. The carriage transports the passengers to the Belle Époque, an era Adriana considers Paris’s Golden Age. Gil and Adriana go first to Maxim’s Paris, then to the Moulin Rouge where they meet Henri de Toulouse-Lautrec, Paul Gauguin, and Edgar Degas. Gil asks what they thought the best era was, and the three determine that the greatest era was the Renaissance. The enthralled Adriana is offered a job designing ballet costumes and proposes to Gil that they stay, but Gil, upon observing that different people long for different “golden ages”, has an epiphany and realizes that despite the allure of nostalgia, any time can eventually become a dull “present”, so it’s best to embrace your actual present. Adriana however, elects to stay in the 1890s, and they part.
Gil rewrites the first two chapters of his novel and retrieves his draft from Stein, who praises his progress as a writer and tells him that Hemingway likes it, but questions why the main character has not realized that his fiancée (based on Inez) is having an affair with a pedantic character (based on Paul).
Gil returns to 2011 and confronts Inez. She admits to having slept with Paul, but dismisses it as a meaningless fling. Gil breaks up with her and decides to move to Paris. Amid Inez’s pique, Gil calmly leaves, after which Inez’s father tells her and her mother that he had Gil followed, though the detective has mysteriously disappeared. It is revealed that the detective found himself in the Versailles of Louis XIV, and is last seen fleeing from the palace guards amid threats of “Off with his head!”
Walking by the Seine at midnight, Gil bumps into Gabrielle, and, after it starts to rain, he offers to walk her home and they learn that they share the love of Paris in the rain.