The movie opens with some beautiful scenes of Paris on a sunny day and on a rainy day. When the credits roll out in standard white on black Woody Allen fashion, you hear the voiceover of couple Inez (Rachel McAdams) and Gil (Owen Wilson). Gil is waxing poetic about how wonderful Paris is and his fiancée Inez is telling him that he’s in love with a fantasy of Paris. They’re at Monet’s garden on a bridge over the lily pond and they share a kiss. They return to their hotel and have dinner with Inez’s parents. Inez’s father is in town on business and Gil and Inez are tagging along with Inez’s mother. Gil is a successful Hollywood screenwriter who is now working on his first novel. He sees his screenwriting work as lacking artistic integrity (he often rewrites bad scripts) but he’s very protective about his novel and doesn’t want anyone to read it. Inez is happy with Gil’s steady screenwriting work and her mother worries that he’ll want to give it up to write. Inez tells her mother than he only talks about giving it up but won’t do it.
During dinner, Inez bumps into an old college friend, the academic Paul and his wife Carol. Paul is a professor who is in town to lecture at La Sorbonne. Inez is obviously very impressed with Paul and Gil is not. They end up going sightseeing with Paul and Carol to the Rodin museum where Paul tries to correct the tour guide (Carla Bruni) over the name of Rodin’s mistress. Later during a wine tasting, Paul ends up being an expert on wine too, much to Gil’s dismay. Paul and Carol invite Gil and Inez to go dancing with them but Gil stays behind and says he wants to get some fresh air. Inez tells him to take a cab home because he’ll get lost. Gil ends up wandering the streets of Paris and does end up getting lost. He tries to ask some Parisians for directions but no one speaks English. He gives up and rests on some steps for a while, watching cars go by in the night. All of a sudden, an old car from the 1920s appears and the people in the car beckon Gil to join them. Gil approaches the car and a man in a tuxedo with a glass of champagne invites him in. Still a little tipsy from the wine tasting, Gil gets in. Everyone in the car is dressed in clothes from the 1920s and the car whisks them away to a party.
At the party, Gil encounters Cole Porter singing and playing the piano. Zelda Fitzgerald (Allison Pill) then approaches him, welcoming him as an American. She then waves over her husband, the writer F. Scott Fitzgerald. Gil suddenly realizes that he’s been transported back in time and is mingling with some of his artistic heroes from the 1920s.
Zelda gets bored with the party and suggests they move on. They attend another party and Gil is still bewildered at the whole idea of traveling in time but then begins to enjoy the moment. Zelda and Scott then bring Gil to a small bistro for drinks and they run into Ernest Hemingway (Corey Stall). Hemingway talks about writing with truth and courage. Gil asks him to read a draft of his novel which is about a shop owner who sells antiques. Hemingway tells him he hates his novel already because if it’s well written, he’ll envy Gil and hate the novel and if it’s badly written, he’ll hate it because of its poor quality. He then offers to have his friend Gertrude Stein look over the novel. Gil is excited and leaves the bistro and then remembers he didn’t arrange a time or meeting place to bring his novel to Hemingway. When he returns to the bistro, Gil is back in the present and the bistro is now a laundermat.
The next day, Gil and Inez do more sightseeing with Paul and Carol, this time to Versailles and some museums. Paul bores Gil with his knowledge of all things cultural. After dinner with her parents, Gil begs Inez to join him on the corner where the 1920s car picked him up. After waiting for some time, Inez gives up and returns to the hotel. Right at midnight, however, the car comes back with Hemingway and he picks Gil up. He meets Gertrude Stein (Kathy Bates) and she agrees to read his manuscript. She introduces Gil to Pablo Picasso and his mistress Adriana (Marion Cotillard). Picasso has just painted an abstract picture of Adriana which Gertrude thinks is too sexual. Gertrude reads the first few sentences of Gil’s novel aloud and Adriana thinks the beginning of Gil’s novel is charming. She reveals that she came to Paris from Bordeaux to study fashion under Coco Chanel. She tells him about all the affairs she’s had with famous artists which led her to Picasso. Gil is fascinated by Adriana but declines when they decide to go out. When sightseeing with Paul at a museum the next day, Gil sees the Picasso painting and provides all the details about Adriana and Gertrude Stein’s interpretation of the painting. Inez is irritated since she considers Paul to be the expert and doesn’t want Gil to contradict him.
The next day while antique shopping, Gil comes across an old phonograph playing an old Cole Porter record. Gil talks with the young Parisian shop girl and makes a joke about knowing Cole Porter. Inez then calls Gil over to show him an expensive antique chair she wants to buy which costs 18,000 euros. Gil remarks that they haven’t bought a house yet and complains about the price. Inez’s mother suggests Gil is cheap and it’s suggested that Inez is a bit materialistic herself. It starts raining and Gil suggests that he and Inez take a walk in the rain, since Paris is beautiful when it’s raining. Inez and her mother are irritated by the rain and run to their car. Gil reluctantly joins them.
That evening, Inez is dining with her parents while Gil is out. She says that she’s going dancing with Paul since his wife is out sick and Gil is busy working on his novel. In the meantime, Gil is out dancing in the 1920s at a party and runs over when he spots Adriana. They bump into Hemingway who declares that he’s going to steal Adriana away from Picasso. Gil and Adriana then leave the party and talk. Adriana has the same nostalgia for the past as Gil, but she’s obsessed with the Belle Epoque, the 1890s of Paris. They then spot Zelda Fitzgerald about to throw herself into the Seine because she suspects her husband is in love with another woman. Gil and Adriana stop her and Gil gives her a valium to calm her down. He then reveals that he’s been taking them because he’s had panic attacks ever since he got engaged to Inez.
They stop at a bar and Adriana decides to end the night there since Gil has a fiancée. As Gil is walking out, Salvador Dali (Adrian Brody) invites him over for a drink and talks about doing a surreal portrait of Gil. Man Ray and Luis Bunel enter the bar and join them. Gil is star struck again and reveals that he’s from the 21st century. This doesn’t faze the others since they are surrealists. Gertrude Stein then gives Gil feedback on his novel and tells him that Adriana has run off with Hemingway to Africa. She doesn’t think it will work out between them and predicts they’ll be back soon.
While sightseeing, Gil ends up buying a Cole Porter record from the antiques shop girl and also buys an antique book from a bookseller along the Seine. The book is in French and ends up being a memoir that Adriana wrote. He asks the museum guide (Carla Bruni) to translate one passage. It’s about Gil and Adriana’s attraction to him and her disappointment that he’s engaged. She says she has a dream where he gives her a gift of earrings and then they make love. That weekend, Inez and her parents are joining Paul in the countryside without Gil. Gil gets ready to see Adriana that night and realizes he doesn’t have any earrings to give her, so he goes through Inez’s jewelry box and re-gifts a pair of pearl earrings for Adriana. Inez and her parents return unexpectedly because Inez’s father has chest pains. A hotel doctor is summoned and then Inez realizes her earrings are gone and reports it as a theft to the hotel front desk. Gil unwraps the gift and pretends to find Inez’s earrings.
The next day, Gil buys some antique earrings for Adriana and returns to the 1920s and finds her at a party. They stroll along Paris at night and he kisses her and gives her the present. He tells her that in that moment of their kiss, he felt immortal. As soon as she puts the earrings on, a horse and buggy pulls up and the occupants beckon Adriana and Gil to join them. The carriage transports them to the Belle Epoque of Paris, Adriana’s favorite time period. They attend a party and then see some cancan dancers at the Moulin Rouge. They meet Toulouse-Lautrec, Paul Gaugin and Edgar Degas. Adriana is star struck and waxes poetic about the Belle Epoque. The artists respond that the golden age was the Renaissance, not their time. She then tells the men that she came to Paris to study fashion and costume design. Degas suggests that she help design costumes for the New York ballet. Adriana pulls Gil aside and she suggests that they stay in this era and never go back to the 1920s. Gil tells Adriana that he’s from a different era and the 1920s is his ideal. He tells her that in every era, people long for and idealize the past. He also goes on about the downsides of the 1890s such as the lack of antibiotics. Adriana reminds him that he regrets not staying in Paris the first time he visited and says that she’s not going to make the same mistake. Gil then realizes that no one is ever really happy where they are in time and space. You will always romanticize another time and another era and he decides to leave Adriana there and return to his own time.
Before he leaves, he stops by Gertrude Stein’s apartment. She has just re-read his revised novel and tells him the Hemingway pointed out that the protagonist should have seen up front that his fiancée was having an affair with the academic. Gil suddenly realizes that he’s been in denial about his suspicious about Inez and Paul.
He returns to the hotel and confronts Inez about her affair. She denies having an affair and tells Gil to come back to modern times instead of living in his fantasy world of 1920s writers and artists. He tells her that he wants to move to Paris and that he’s not going back to California (and presumably will give up his lucrative screenwriting career). That’s the end of their relationship since Inez doesn’t want to move to Paris. Inez’s parents return and tell Inez that the detective they hired to follow Gil has disappeared. We then see the detective has traveled back in time to the days of Louis XIV at Versailles and is chased by guards in the Hall of Mirrors when he interrupts Louis’s breakfast.
Gil is strolling around Paris at night and the Eiffel Tower sparkles with lights in the distance. He then bumps into the Parisian shop girl who sold him the antique Cole Porter record. She says she thought of him because they just received a new shipment of Cole Porter records. He tells the girl he’s decided to stay in Paris and invites her to take a walk. It starts to rain but the girl says she doesn’t mind the rain since Paris is still lovely in the rain. Gil agrees and they walk in the rain together.
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