Gil, portrayed by Owen Wilson, is a celebrated yet distracted Hollywood screenwriter. During a trip to Paris with his fiancée, Inez, played by Rachel McAdams, and her affluent, traditional parents, Gil finds himself torn between his aspirations and the dismissive attitudes of his loved ones. While Gil is passionately attempting to finalize his debut novel about a man who runs a nostalgia shop, Inez and her parents remain unsupportive, urging him to continue his profitable career in Hollywood. As Gil contemplates a permanent move to the enchanting city of Paris, Inez remains committed to the idea of a life in Malibu.
The dynamic shifts as a chance encounter brings Inez's friend Paul, portrayed by Michael Sheen, into the mix. A self-proclaimed intellectual, Paul captivates Inez but irritates Gil, who reveres the Lost Generation. When a night out dancing is proposed, Inez enthusiastically agrees while Gil opts to explore the mesmerizing streets of Paris alone. Lost and reflective at the stroke of midnight, he is drawn to an antique car reminiscent of the 1920s, where elegantly dressed passengers beckon him to join their revelry.
Once inside a lively bar, Gil soon realizes he has traveled back in time to the vibrant 1920s—an era he deeply admires and incorporates into his writing. There, he encounters literary giants such as Cole Porter, Josephine Baker, and the Fitzgeralds, Zelda and F. Scott, played by Alison Pill and Tom Hiddleston. These iconic figures introduce him to Ernest Hemingway, essayed by Corey Stoll, who offers to review Gil's manuscript. Excited yet nervous, Gil leaves the bar to retrieve it, only to find himself abruptly back in 2010.
Determined to share this extraordinary experience, Gil invites Inez to join him the following night, but her impatience leads her to abandon their rendezvous. Undeterred, when the clock strikes midnight again, Gil finds Hemingway waiting for him. This time, he is brought to meet Gertrude Stein, portrayed by Kathy Bates, who agrees to read his novel, introducing him to the renowned painter Pablo Picasso and his enchanting mistress, Adriana, played by Marion Cotillard. Instantly captivated by Adriana, Gil feels a burgeoning connection.
The following day, back in 2010, Gil views a painting of Adriana at a museum, impressively narrating its backstory. His passion, however, frustrates both Paul and Inez, who doubt his credentials and belittle his interests, much to his chagrin. As his nocturnal escapades in the past grow more frequent, Inez grows suspicious and frustrated, leading her father to hire a detective to shadow Gil. Unfortunately for the detective, his efforts are futile, as he becomes hopelessly lost in the past.
As time unfolds, Gil and Adriana's bond deepens, complicating Gil's emotions. Seeking advice from avant-garde figures like Salvador Dalí and Luis Buñuel, they dismiss his time-traveling predicament as quite normal. One day, while Inez is busy shopping, Gil encounters Gabrielle, an antique dealer who shares his appreciation for the 1920s.
Upon discovering a diary belonging to Adriana, Gil is struck by the realization that she harbors feelings for him, seeing the desire for gifts that are deeply personal. He initially attempts to steal some earrings from Inez to gift to Adriana but is caught in the act. Ultimately, Gil decides to purchase a pair of earrings, reviving his pursuit of true love. Upon confessing his feelings to Adriana, their kiss leads them into a lavish horse-drawn carriage, transporting them to the majestic Belle Époque—a time that Adriana considers Paris's true Golden Age.
At Maxim's Paris restaurant, they meet luminaries such as Henri de Toulouse-Lautrec and Edgar Degas, leading to a spirited conversation about historical greatness. When invited to stay in the past, Gil ultimately chooses to embrace the present rather than survive in mere nostalgia. Heartbroken, he parts from Adriana as she opts to remain in the past.
Returning to the present, Gil retrieves his manuscript, only to receive a critical yet encouraging response from Gertrude Stein, who remarks on the parallels between his character and Inez, suggesting infidelity. Confronting Inez reveals her affair with Paul, which she nonchalantly suggests can be ignored once they return home. In a moment of clarity, Gil breaks free from their relationship, deciding to stay in the vibrant city of Paris where he unexpectedly encounters Gabrielle once more, reigniting hope as they stroll together at midnight.
