Director: Woody Allen
Stars: Owen Wilson, Rachel McAdams, Kathy Bates, Kurt Fuller
Gil (Owen Wilson), a successful but distracted Hollywood screenwriter, and his fiancée, Inez (Rachel McAdams), are in Paris, vacationing with Inez's wealthy, conservative parents (Mimi Kennedy, Kurt Fuller). Gil is struggling to finish his first novel, which is about a man who works in a nostalgia shop, and Inez and her parents are critical and demeaning of Gil's decision to give up his lucrative Hollywood career. They do not share his romantic view of Paris, and while Gil is considering moving to the city for inspiration, Inez is intent on living in Malibu. By chance, they are joined by Inez's friend Paul (Michael Sheen), a pseudo-intellectual who speaks with great authority but little actual substance or accuracy on the history and art of the city. Inez idolizes him but Gil, who is an ardent admirer of the Lost Generation, finds him insufferable.
After a wine tasting, Paul and his wife Carol (Nina Arianda) invite Inez and Gil to go dancing. Inez accepts but Gil, sick of Paul and a little drunk, declines and chooses to walk back to their hotel through the streets of Paris, eventually becoming lost. As he stops at a set of stairs, the midnight bells ring and an old-fashioned car pulls up at the corner and he is invited to join a group of fancily-dressed, champagne-drinking party-goers. They go to a bar, where to his shock, Gil discovers he has been transported to the 1920s, an era he admires and idolizes in his to-be-novel. He encounters Zelda and F. Scott Fitzgerald (Allison Pill and Tom Hiddleston), who take him to meet Ernest Hemingway (Corey Stoll). Hemingway agrees to show Gil's novel to Gertrude Stein (Kathy Bates), and Gil goes to fetch his manuscript from his hotel. However, as soon as he leaves the bar, he is suddenly transported back to 2010.
Gil attempts to show Inez how he traveled into the past, but she refuses to believe him and peevishly returns to their hotel. Just after she leaves, the clock strikes midnight and the car pulls up again with Hemingway inside it. He takes Gil to meet Gertrude Stein, who agrees to read his novel and introduces him to Pablo Picasso (Marcial Di Fonzo Bo) and Picasso's mistress Adriana (Marion Cotillard), a strikingly beautiful student of couture to whom Gil is instantly attracted. The next day, back in 2010, Gil encounters Picasso's painting of Adriana at a museum, allowing him to show up Paul with intimate knowledge of the work.
Over the next few days, Gil spends each night in the past, telling Inez that he is wandering the streets getting inspiration for his novel. His late-night wanderings frustrate Inez and arouse the suspicion of her father, who hires a detective (Gad Elmaleh) to follow Gil. This proves unsuccessful, as the detective attempts to follow the car and winds up lost in the court of Louis XIV.
Gil spends increasing amounts of time with Adriana, who leaves Picasso and has a brief dalliance with Hemingway. Gil realizes that he is falling in love with her, leaving him increasingly conflicted and confused. He confides his predicament to Salvador Dalí (Adrien Brody), Man Ray (Tom Cordier) and Luis Buñuel (Adrien de Van), but being surrealists they consider his position to be totally normal and see nothing strange about his coming from the future.
While Inez shops for furniture at a street market in 2010, Gil connects with Gabrielle (Léa Seydoux), an antiques dealer who shares his fondness for the twenties. While there, he discovers Adriana's diary from the 20s in a used book stall, and, after receiving the aid of a friendly tour guide at the Rodin museum (Carla Bruni) to translate it, finds out that she was in love with him. Reading that she dreamt of receiving a gift of earrings from him and then making love to him, Gil attempts to steal a pair of earrings from Inez to give to Adriana but is thwarted by her early return from a trip.
Gil purchases earrings for Adriana and, returning to the past, confesses his love for her. As they kiss on a deserted street, a horse and carriage appear. They are invited inside by a richly-dressed couple and are transported to the Belle Époque, an era Adriana considers Paris' Golden Age. They are taken to the famous Maxim's Paris club, and meet Henri de Toulouse-Lautrec (Vincent Menjou Cortes), Paul Gauguin and Edgar Degas (François Rostain). The enthralled Adriana is offered a job designing ballet costumes, and proposes to Gil that they stay, but Gil realizes that despite the allure of nostalgia, it is better to accept the present for what it is. Adriana elects to stay in the past, and they sadly part ways.
Gil retrieves his novel from Gertrude Stein, who praises his progress as a writer but questions why the main character has not realized that his fiancee (based on Inez) is having an affair with a pedantic character clearly based on Paul. Gil returns to the present and confronts Inez. She admits to sleeping with Paul but claims that it can be forgotten when they return to California. Gil breaks up with Inez and decides to remain in Paris. Taking a walk at midnight, he unexpectedly meets Gabrielle, and offers to walk her home, indicating that they will start a relationship.
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