Pooh Bear brings a tricycle to his playdate with Piglet, but Piglet is too afraid to ride again having fallen off once before. To teach Pooh, Piglet must try, try again.
Pooh Bear brings a Jar to his playdate with Piglet. There is just one thing, he doesn't know what's inside!
Pooh Bear is excited to share his harmonica with Tigger, but Tigger is too full of energy to sit still and play. Pooh Bear must play a tune for Tigger to get his bounces out.
Pooh Bear brings a cardboard box to his playdate with Piglet, teaching him that the box can be anything if he uses his imagination.
Kanga teaches Pooh Bear how to play Hide-and-Go-Seek but when Pooh Bear hides he gets the hiccups and is found. Pooh Bear is sad, but then he learns it's his turn to seek now.
Pooh Bear brings a paint set to his playdate with Eeyore. Eeyore finds a butterfly he wants to paint but doesn't have the right colors so Pooh Bear teaches him how to mix colors!
When Pooh Bear brings a kite to his playdate with Piglet, both of them have a hard time flying it. They figure out they can fly the kite by working together!
Pooh Bear and Eeyore go on a treasure hunt. They get stumped on their last clue, but after some encouragement, Eeyore figures it out and they find the treasure!
Pooh Bear teaches Tigger how to keep a hoop from falling to the ground. Pooh Bear tells Tigger that the most important part of trying a new thing is practicing.
Pooh Bear realizes the chalk he brought has turned to dust so Rabbit hops home to get a spare box. Pooh Bear gets bored while waiting for her to return and makes up some games.
Pooh Bear and Piglet make a snow bear together. After they're done, Pooh Bear and Piglet worry that the snow bear will get lonely so, they make a snow pig so that it has a friend.
Pooh Bear brings a bouncy ball to his playdate with Tigger. Tigger suggests a game called 'Big Bounce' and bounces the ball so hard that it almost gets stuck in the tree.
Pooh Bear, Rabbit, and Piglet are having a picnic together. Rabbit brought avocados that she grew in her garden to share, but Piglet is nervous to try a food he hasn't had before.
Pooh Bear and Bea build a pillow fort together at their playdate. But oh no! When they finish building it, they find that it has no doors to go inside.
Kanga brings a blank book to his playdate. Kanga explains that they are gonna fill the book up with their own story. Together Pooh Bear and Bea come up with a story.
Winnie the Pooh brings a music box to his playdate with Tigger and Kanga. They're having a dance party!
Winnie the Pooh and Piglet bring their new sleeping bags to a playdate. They're having a sleepover at the Treehouse!
Winnie the Pooh brings a flying disc to his playdate with Eeyore. When Pooh Bear has to go home to eat and rest, Eeyore feels sad.
Winnie the Pooh brings a pitcher for his playdate with Rabbit. They're going to set up a lemonade stand!
Winnie the Pooh brings a trampoline to his playdate with Tigger so they can bounce around together.
Pooh Bear takes Eeyore trick-or-treating for the first time! When they set out and trick-or-treat, Eeyore realizes there is a hole in his bag.
Winnie the Pooh joins Rabbit and Bea for their playdate. Rabbit has grown a pumpkin, and they will turn it into a jack-o'-lantern for Halloween!
Winnie the Pooh brings a toy boat to his playdate with Eeyore so they can pretend to be pirates and send the boat down the creek in Hunny Hollow.
When Winnie the Pooh brings a box of ornaments to decorate a Christmas tree, Pooh Bear and Piglet must find the perfect tree!
Winnie the Pooh and Piglet meet on Christmas morning to finish making their crafted Christmas tree and just in time as they run out of glue.
