A mysterious hat floats onto Doug's head. Strange and wonderful things begin to happen to him so Doug claims the hat as lucky, and it isn't long before Roger wants to get his hands on it.

Doug's Bluff Scout Troop #617 has to raise money for new canoes, so they sell ""Bluff Scout Booster Bars"" door to door. But after being rejected by everyone, Roger offers a new way to sell the bars, which Doug doesn't agree with. Then when Doug sells a bar to Mr. Swirly, he realizes the problem of why the bars taste so horrible.

Over the weekend, Doug puts on a few pounds at Grandma Funnie's house and has been invited to Beebe's pool party. Doug is so embarrassed to be seen in a swimsuit, so he decides to work the extra weight off before the party using Ronald ""Prepare to Suffer"" Weisenheimer's videos.

It's the day of the big football game against Bloatsburg and Doug is snared by Coach Spitz, who mistakenly believes Doug has a ""golden toe"" for field kicking. Doug is then put into the next footbal game by Coach Spitz, and he is very nervous when he finds out that Percy Femur is on the other team.

Roger tricks Doug into breaking a school rule which causes Mr. Bone to give his entire class a detention on a Saturday. Doug imgaines how Quailman would handle the situation of battling the Rulemeister and his pointless rules to try and get his friends out of detention.

Phil convinces Doug that he has a great idea to build the perfect kite to compete in the upcoming Bluffscout airshow. But Doug thinks his Dad's idea is too simple, so he changes it thinking it will be better, but he gets surprising results.

Doug is accused of cheating when he and Chalky score identical marks on a test. He is given one day to confess or he'll have to take a re-test. Doug knows he didn't cheat so he tries to talk about it with Chalky, but he keeps avoiding Doug.

Patti asks Doug to go with her to the movies, and now everyone at school is teasing them about dating. Even Doug wonders if it is really a date or not. In order to find out, Skeeter goes through dating scenarios from a book with Doug.

A/B) When a spooky new amusement ride, Blood Stone Manor, opens up at Funkytown on Halloween night, Skeeter wants to check it out instead of trick or treating. Doug reluctantly agrees to go, but when the park closes before their turn comes up, Roger convinces them to go on the ride anyway. Once on the ride, Roger scares Doug and Skeeter big time, so it's up to them to scare Roger back!

Doug wishes he was more fashionable until his friends at school accuse him of dressing like Dylan Farnum from the TV show ""Teen Heart Street"". He's tired of being told he's copying someone else's style, so he decides to shop for a new look.

After performing a magic trick, Doug becomes adored by a third grader named Todd Bentley, who starts to follow Doug everywhere. Soon Doug is embarrassed by all the attention Todd is giving him, and tells Todd to leave him alone, which upsets Todd and leaves Doug feeling guilty.

A prankster steals Vice Principal Bone's ""Der Grosser Yodelmeister"" Trophy, and puts it in Doug's locker. Mr. Bone searches all the school's lockers and is convinced that Doug had stolen the trophy.

For Student Government Day, Doug is chosen to interview the Mayor of Bluffington, Mr. Robert ""Bob"" White. He visits the mayor on a field trip to Bluffington Town Hall, and saves the ice cream factory from a meltdown.

Beebe brings her new expensive radio to school, in order to impress the other students. When it ends up missing, Mr. Bone threatens to hold the whole class in afternoon detention, if the radio is not returned. Hoping to catch the real culprit, Doug decides to take the case as ""The Chameleon"", who is a master of disguise. But when Doug finds out that Skeeter has the radio, he'll either have to turn him in or cover for him

Doug writes a secret love song about Patti, and makes it into a video at a new store in the mall where you can make your own music videos. But after a mix up at the store, Doug gets Mr. Bone's video and Doug thinks his tape fell into the hands of Patti who is taking it to a slumber party at Beebe's house.

When Porkchop begins acting very strangely, Doug tries to find out what's causing his friend's odd behavior. It turns out that Porkchop has come down with a case of ""puppy love"" for a local poodle.

Doug refuses to get his picture taken for School Photo Swap Day at school, because he has suddenly become self-concious of his nose after Skeeter's brother Dale calls Doug ""big nose"".

Doug is entered (thanks to Roger) into a school talent contest, and decides to try out a ventriloquism act. Once their on stage, Doug has to keep his new pal Buster from losing his head on stage.

Doug is excited when his Aunt Betty-Ann invites Skeeter and him to be on a TV show. The only problem is that it's the kiddie show ""Kiddie Koral"". Doug's goes to the kiddie show with Skeeter and later regrets it when Roger sees him on the show and tapes it. But when Betty-Ann recognizes Roger, the embarassement tables are turned.

An exchange student from Yakestonia named Fentruck Stimmel comes to live in Bluffington and attend the Bluffington School. But after Fentruck asks Doug to help him write a letter, Doug begins to suspect that the new kid may have eyes for Patti.

Roger asks Doug to take care of his cat, Stinky, while he goes on a trip. Stinky not only rips up the Funnie home but also eats all the junk food in the house and gets sick. Doug rushes him to the vet, hoping he'll be OK. But when Doug gets there, he finds out Stinky isn't a ""he"".

Someone has sabotaged the wheelbarrow race at the Bluffington picnic and now no one can be in the race. So, Doug and Patti team up to solve the mystery of who did it and why.

Judy catches Doug breaking a vase that belonged to their mom. To keep her quiet, Doug must agree to be her slave for a week. He suffers until he realizes that the only way out is to tell the truth.

Doug was only defending himself when he punches Larry the AV nerd in the face because Doug thought he was making fun of him. Now he's popular because of his fight, but Doug can't stand that he punched Larry and wants to be friends again. But everyone likes Doug for it and his popularity could disappear.

Doug is invited to Beebe's party, but something shows up on his that face makes it impossible for him to go out in public.