The story centers on Robin, the adult version of the boy who in the A.A. Milne books shares his adventures with the animals of the Hundred Acre Wood. Robin has grown out of the joyful imagination he had as a young boy and is now a businessman who prioritizes work over his wife and daughter.

With his home life on the brink, the last thing his life needs is the return of Pooh, who needs his help in finding his friends again. Robin has to find a way to help both sides or risk losing everything he holds dear.