The ending scene after the "Tigger Too" chapter, where Christopher Robin and Pooh discuss what they liked doing together and the boy asks his bear to promise to remember him and to keep some of the memories of their time together alive. Pooh agrees to do so, and the film closes with The Narrator saying that wherever Christopher Robin goes, Pooh will always be waiting for him whenever he returns.
Creepy or not, the winking Pooh doll at the very end of the film is meant to symbolize that Pooh will always be there for Christopher Robin.
Winnie the Pooh and the Blustery Day
Piglet giving up his beloved house to Owl. Despite everyone attempting with some shrewdness to tell Eeyore his mistake, Piglet informs everyone tearfully the house belongs to his good friend, Owl.
Piglet:(walking off by himself, sniffling and wiping his eyes with his bib) W-well...I guess...I shall live...I suppose...I shall live...
Pooh:(catches up to him and takes his hand) With me. You shall live with me. Won't you, Piglet?
Pooh then asks Christopher to "make a one-hero party into a two-hero party", so that Piglet can share the party with him as well.
Winnie the Pooh and Tigger Too
When Rabbit's plan to get Tigger lost in the Woods to scare him backfires into getting himself lost, Tigger, regardless of the circumstances, immediately volunteers to find him and bring him home, which he does.
Kanga sending Roo and Tigger off to play and Tigger assuring her he'll watch out for Roo.
When Tigger refuses to break his promise to never bounce again, he very sadly trudges away. Everyone else, despite so direly wanting rid of Tigger's annoying bouncing habit before, is instantly heartbroken by this sorry sight, and want the old bouncy Tigger back (even if Rabbit takes a little coercing).
Following this Tigger, immediately bounces back in frame overjoyed, and convinces Rabbit to try bouncing with him. Rabbit actually finds himself enjoying bouncing and soon everyone is bouncing along to a triumphant reprise of "The Most Wonderful Thing About Tiggers". The sight of Tigger and Rabbit bouncing and laughing together is priceless.
Winnie the Pooh and a Day For Eeyore
Pooh and Piglet attempt to get gifts for Eeyore's birthday, though things expectedly go wrong. Piglet mournfully hands Eeyore his now popped balloon, while Pooh hands him his now empty pot of honey. Despite the pitiful nature of both gifts, Eeyore still spots some practicality in them and beams, for the first time in the franchise, a warm earnest smile.