Welcome to Valentine

Olivia Lafferty is a struggling artist in New York City working as a cater waiter to make ends meet. Her life takes a downward turn when her roommate, Tess, books an acting role in Chicago and must move out, leaving Olivia without an apartment. At a high-profile art event, Olivia attempts to show her portfolio to gallery owner Camilla Hollander, but the encounter ends in disaster when she spills mushroom soup on the mogul and gets fired. Tess suggests that Olivia join her and her distant cousin George on a road trip west. George, the heir to a major investment firm, is driving his grandfather’s vintage car, 'Big Red,' to Los Angeles for his inauguration as CEO. George is a rigid pragmatist with strict rules against food or drink in his car, leading to immediate friction with the more free-spirited Olivia. After dropping Tess off in Chicago, George and Olivia continue to Valentine, Nebraska. Upon arrival, George intends to drop Olivia off and keep driving, but a local mechanic named Ronald accidentally fries the car's electrical system while trying to help. Stranded in a town that treats Valentine's Day like a 'marathon,' George stays at Barbara May’s diner and inn. He initially scoffs at the town's simplicity but quickly becomes a local celebrity after buying strawberry milkshakes for the entire diner. Meanwhile, Olivia helps her sister Vanessa, the new parade coordinator, deal with the pressure of succeeding the formidable Miss Hacky. As George waits for parts, he helps Olivia scavenge for materials for the parade floats. During their time together, George discovers Olivia’s talent through her sketchbook and encourages her, while Olivia challenges George to pursue the philanthropic business ideas his father previously dismissed. A 'pre-truth'—a lie George told to make Olivia look successful to her old friends—initially causes tension but eventually leads Olivia to be honest about her struggles. George eventually fixes his car using a part from an old float provided by Miss Hacky. He leaves for his board meeting in LA but realizes he cannot return to his old life. He pitches a new philanthropic arm to his board via a conference call from the road and returns to Valentine just in time for the parade. The film concludes with Olivia finally achieving her dream of being represented by the Hollander Gallery, specializing in art inspired by her hometown.