When Beebe Bluff's radio mysteriously disappears after show-and-tell, Doug, imagining himself as disguise-master sleuth, "The Chameleon," takes up the case. At the new "make your own music video" store, Doug makes a video of a love song he wrote about Patti only to regret it later.
Doug saves up for weeks to buy Patti a beetball for her birthday--only to blow all his money on a video game. Roger invites everyone to his house except Doug. After consulting with Quailman, Doug bravely goes to the party to confront Roger, and walks right into a surprise party celebrating Doug's first year in Bluffington.
Doug is geting notes from a secret admirer. His first guess is Patti but then finds out it's Beebe! He decides to let her down easy, only to find out that Skeeter is the object of her affections. Doug's aunt Betty-Ann is a TV producer and she has a special present for him: tickets to Kiddie Corral!
Doug is thrilled when Patti invites him to dinner until he finds out that liver and onions will be served. He tries everything, including hypnosis, to finally overcomes his phobia of the dish, only to find out that Patti was only kidding. Doug befriends the new kid in town, Yakkestonian exchange student Fentruck Stimmel, and helps him write a letter in English.
Judy's in charge of this year's production of the annual pageant, and she asks all of the kids to participate in rewriting the play. Roger is acting strangely. . . nice! Doug is mystified, and his confusion turns to horror when he figures out why: Roger has fallen for Judy, but Doug's biggest worry is has Judy fallen for Roger!
All the kids are building soapbox racers for the Mt. St. Buster Downhill Speed Race, and the competition has everyone at each other's throats. It takes a disaster to remind everyone that helping a friend is more important than winning. Doug's parents go to Judy's school dance and Doug plans a rock-n-roll evening in the house by himself.
Roger tricks Doug into breaking a school rule and Lamarr Bone sentences the class to Saturday Detention. Doug turns to Quailman for advice and in the end triumphs, discharging all of the kids from detention. Doug is furious at Porkchop for tracking paw-prints all over his entry in the Arts Guild Exhibition. But everyone thinks his ruined painting is a brilliant piece of modern art!
Roger prepares his spitballs, "kick me" signs and bully attitude for the new kid in school. But when the new kid turns out to be twice the size of Roger, Doug must defend Roger for a change! When the kids criticize Mr. Bone's dull school-news video show, he makes the mistake of challenging them to do a better one.
To get out of going to the Hoedown with Connie, Doug says he is staying home to take care of his sick cousin, "Melvin." His lie gets him into big trouble when Patti and Connie come over to visit his patient. Doug signs up to be the lead dancer in the school ballet so he can be partners with Patti.
The Bluffscout canoe trip runs into trouble when Scoutmaster Dink heads off to fix his broken computer, leaving Roger in charge. Just when Doug has persuaded The Beets to play a concert at school, Mr. Bone nixes the deal. After consulting Quailman, and battling a robotic army of Assistant Principles, Doug designs a compromise that has Mr. Bone jumping for joy.
Competing in the Mayor's fitness test is going to be no picnic for Doug who is ironically out of shape. He embarks upon a crash exercise program to prepare and only succeeds in hurting every muscle in his body. A hot-shot movie director is talent hunting in Bluffington and everyone is sure they will be chosen, especially Judy.
The Beets concert is sold out, but Doug finaggles two tickets out of his sister. He and Skeeter set out on an incredible adventure where they end up as emergency Beets roadies. Doug has a cavity and must go to the dentist. Although he dreads the appointment, and fantasizes how Secret Agent Smash Adams would handle the situation, his frown turns to a smile when he meets his new female dentist.
Doug is thrilled with his new video game but the more he plays, the more he can't put it down. Crisis hits when he realizes the weekend is over and his homework isn't done. Doug can never find a hat that fits him just right until one day a mysterious hat flies into his life. Strange and wonderful things begin to happen to him, and it isn't long before Roger is scheming to get his hands on it.