While trying to find somebody to play with, Tigger gleefully bounces around the Hundred Acre Wood, disrupting his friends’ attempts to prepare for the winter and accidentally causing a huge rock to fall on Eeyore’s house. Rabbit leads the others with a highly over complicated plan in trying to remove it with an elaborate pulley system (which collapses) and Tigger intervenes, knocking the rock away with his Whoopty-Dooper-Loopty-Looper-Alley-Ooper bounce and getting everyone covered in mud and mad at him, particularly Rabbit, who is annoyed that his pulley system was ruined by Tigger’s bouncing. Feeling alone, Tigger sulks on a bridge and Roo, trying to cheer him up, asks if there are other Tiggers. Fascinated by the idea, Tigger talks to Owl, who explains about family trees. Tigger, taking this literally, heads out to find a huge stripey tree and, after not finding one, instead writes a letter to his family. No reply comes and Tigger feels more alone then ever.
That night, everybody gathers at Piglet’s house. Feeling sorry for Tigger, Roo announces that they should write a letter to him. Roo then slips the letter into Tigger’s letter box. The next day, everybody is woken by Tigger, who brandishes the letter. He shouts joyfully that his family has written to him and also that they are coming to visit the next evening. They are all shocked, as they had never written down anything that even resembles that; nevertheless, Tigger replies that he always reads between the lines. Later, Roo gathers Pooh, Piglet, Owl and Eeyore over to his home. He and his mother Kanga say they are going to charade as fellow Tiggers to attend the party and make Tigger feel loved. Meanwhile, Tigger is preparing for his party when somebody rings the doorbell. He opens the door to reveal a large number of Tiggers who claim to be his family. A party ensues with drinks, dance and games, and all the while Tigger believes they are his family. Yet when the smallest (Roo) attempts the Whoopty-Dooper Loopty-Looper Ally-Ooper Bounce and his mask falls off, the others reveal themselves as Tigger’s friends. In despair, now sure that he must truly be the One and Only, he leaves the room, stating that he is leaving forever. He hikes through the snow until he finds a large tree on the cliffside which matches the description he gave of his family tree. He bounces across the branches, finding nothing, so he sits there, waiting for his family.
Meanwhile, Pooh, Roo, Piglet and Eeyore mount an expedition to find Tigger. When they find him, they tell him to return home, with Rabbit saying he should “Forget about all this other Tiggers nonsense”. Tigger is greatly offended by them, but when a sudden avalanche caused by his irate shouting occurs, he pulls them all out of trouble. Unfortunately, Tigger himself is still caught in the avalanche. Roo remembers the Whoopty-Dooper Loopty Looper Ally-Ooper bounce and travels down through the rock and snow to Tigger and wakes him from unconsciousness. To get out of the avalanche, they perform the signature bounce together. When everyone tells Christopher Robin why Tigger left, Christopher tells Tigger he didn’t have to leave to find his family. Tigger finally comes to realize what was true all along, that his family is right here and always has been: his friends. Once they return home, Tigger gives everyone gifts. He gives Roo his heart pendant, but it’s still empty. As the movie ends, Christopher Robin remedies this by taking a picture of Tigger’s “family”.