When Pee-wee's robot, Conky 2000, breaks down, the Playhouse gang suddenly doesn't feel so "great." When Pee-wee tries to fix the sick robot, Conky winds up in a million pieces! What'll Pee-wee do, now? Call the Authorized Conky Repairman - that's what. Will the repairman be able to fix their pal, or will lovelorn Miss Yvonne wrench him away first?

Everyone better start looking "around" because some of Pee-Wee's favorite possessions are missing! When Miss Yvonne offers to take his suits to the cleaners, Pee-Wee can't find them. Soon, he discovers that his spoon, cereal bowl, and even his connect-the-dots are gone! When the culprit is revealed, Pee-Wee discovers more than just his treasured possessions; he discovers a new friend and a valuable lesson about being yourself!

Pee-wee's revving up the presses to print the Playhouse's first newspaper! The Playhouse crew starts researching their articles with the five "W's" and "H": who, what, when, where, why, and "how." When Pee-wee puts the paper to bed, and then goes to bed himself, sneaky Randy changes everyone's stories to lies! How will the Playhouse pals live it down?

Mrs. Rene is learning how to tango! With a rose in her mouth and Pee-wee's magic footprints on the floor, she dances up a storm until Pee-wee dips her right out the Playhouse door! Cowboy Curtis remembers his first and last whirl on rollerskates, and Jambi helps Pee-wee relive the whole show with a replay that goes by all too "fast."

Because Cowboy Curtis, Miss Yvonne, and Cowntess all have to work, Pee-wee and the Playhouse crew create a special holiday: "Playhouse Day!" To celebrate, they decorate a tree, the Playhouse, and even the King of Cartoons! When they find out it's an official holiday, Cowboy Curtis, Miss Yvonne, and the Cowntess take the day off. After all, it is the fun "thing" to do!

Mrs. Rene stops by to give Pee-wee a letter from a faraway "place" - Japan! It's from Oki Doki, a young Japanese man who soon appears at the Playhouse door. By introducing Pee-wee to sushi, origami, and Gamara, Oki proves that he has a lot to share about his homeland, and Pee-wee has a lot to learn!

Miss Yvonne teaches the gang how to make cheese balls, and Pee-wee makes a mobile. The fun goes "on" and on!

Pee-wee goes on a camping trip with Cowboy Curtis and leaves Mrs. Rene to house-sit the Playhouse. Pee-wee and Cowboy Curtis ride horses, roast wieners, and sleep under the stars. Curtis does his best to "show" Pee-wee a good time, and Pee-wee thinks Curtis is lucky to be a cowboy!

Pee-wee can't figure out what to "do" today, so Jambi gives him a to-do list which includes blowing a big balloon, dressing up as a pirate, and going for a walk with Miss Yvonne. The list also mentions cleaning up Pee-wee's room.