Christopher Robin goes to a boarding school so his friends in Hundred Acre Wood – Winnie the Pooth, Tigger, Piglet, Eyeore, Kanga, Roo, Owl and Rabbit – give a goodbye party. Christopher consoles Pooh and tells him he will never forget him. After a dramatic incident, Christopher has to mature earlier. When he arrives, he moves to London, meets and marries an architect named Evelyn who gives him a little girl named Madeline.
He did his military service during the Second World War. After the war he engages himself, and because of the soliciting service, he gets to neglect his family, planning to send Madeline to a boarding school like he was. When the company gets into a difficult situation, Christopher’s head, Giles Winslow, tells him to do it in a way to reduce all spending by about 20%, meaning downsizing, and take them in a few days a restructuring plan.
This affects Christopher hard, but all the while Pooh wakes up and fails to give his friends, so he decides to cross the door of Christopher’s door and finds himself in London. He meets Christopher, and the latter is shocked to meet him, but he still takes him home to him. After a night and a morning of chaos, Christopher accompanies Pooh back to Sussex on a train trip.