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.
Pooh Bear and Kanga fly a plane around the treehouse until they go to picnic area for a snack. After their snack, they return to play but the plane is missing!
When Winnie the Pooh brings a bubble wand to his playdate with Bea, they make one big bubble!
When Pooh Bear brings an ice cream cake to the surprise party for Eeyore's birthday, the cake begins to melt!
Winnie the Pooh brings hunny pots to his playdate with Bea so they can make an obstacle course for Bea's remote-control car!
Pooh and Bea can't find their caterpillar friend but Rabbit tells them that it must be changing into a butterfly.
Pooh Bear and Piglet play an energetic game of tag. After a while, they start feeling tired. As they take a break, they realize cooling down brings their energy up to play again.
Pooh Bear brings crayons to his playdate with Piglet to draw, but they're missing many colors. They use their imagination and creativity to draw colorful versions of the Treehouse.
Pooh Bear and Piglet are going to make sock puppets for their playdate! They use buttons, bottle caps, and bendy straws to make a sock puppet out of a paper bag.
Pooh Bear brings building blocks to his playdate with Bea. They build a tall tower, but when Bea is too small to reach the top, Pooh Bear finds a solution so Bea can keep playing!
Pooh Bear and Tigger have fun camping in their tent. Tigger has a hard time falling asleep since he's excited for the fun tomorrow, so Pooh Bear sings him a lullaby to go to bed.
Pooh Bear, Tigger, and Rabbit go apple picking. Tigger gets so many apples he doesn't know what to do with them all. Rabbit shares all the yummy foods you can make with apples.
Pooh Bear, Piglet, and Eeyore bring their favorite toys for their playdate. Eeyore learns his rock is just as cool as Pooh Bear's truck and Piglet's unicorn.
Pooh Bear brings a toy train to his playdate with Bea. They learn to take turns being the track builder and conductor, so no one is left sitting around.
Pooh Bear and Kanga play a game of I Spy in Hunny Hollow. When Pooh Bear struggles to spot the red object, Kanga helps by offering a hint.
Pooh Bear teaches Tigger and Eeyore a new game called Jumps on Stumps. When it's Eeyore's turn, he is nervous, but Tigger's cheering motivates Eeyore to finish the game.
Pooh Bear and Rabbit decorate invitations with their new garden stickers for their garden party. When they run out of stickers, they make new ones using tape and markers.
Pooh Bear and Bea have a fun time playing with their toy trucks. They want to keep playing but the floor is too messy. Together they clean up with the help of their toys.
Pooh Bear and Tigger discover their superpowers to save the day from the evil Quacko. While Tigger's power is super bouncing, Pooh Bear discovers his super hugs, rescuing Tigger.
Pooh Bear brings sprinkles to his playdate with Rabbit so they can decorate cupcakes. Rabbit teaches the steps to decorate and reminds Pooh Bear it doesn't have to look perfect.
Eeyore is disappointed that he and Pooh Bear can't go swimming in the creek since it's raining outside. Pooh Bear thinks of a fun indoor underwater adventure that Eeyore loves!
