Doug gets a letter from his school and panics when he sees it's addressed to his parents. Since he's doing poorly in math, Doug immediately assumes that it's a failing notice! So he does everything to find out what the letter says and avoid his parents from seeing it. If that wasn't enough, Patti is trying to tell Doug something and get her message to him.

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.

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.

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.

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.

Doug becomes the victim of a contest scam that promises to make him rich. But after trying so hard and paying a lot of money, Doug later realizes he may not be as close to winning as he thinks.

Doug is impressed by Mr. Bluff's gifts to Beebe. Phil feels pressured to make more money for a better birthday present for his son, so he decides to start his own photography store. At first, Doug is excited by the thought of more money, but when he sees the effects on his father and their family, he realizes that money can't buy happiness.

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.

Doug is nominated for class treasurer, and when he finds himself running against Willy White, the mayor's son, he starts making promises to his voters he knows he can't keep. Meanwhile, Tippi Dink runs for Mayor of Bluffington and wins!

Doug beats Patti in a bowling match, and Skeeter tells everyone about it. Doug gains popularity, but feels bad about beating Patti everytime they play a game. It seems Patti is having a losing streak and is upset about it.

Doug and Skeeter go digging for artifacts when they get assigned to research Bluffington's history. They soon get into trouble though, when they are caught digging on the Bluff estate even though they didn't know.

Skeeter gets a high score on an intelligent test making him a genius, and Doug is convinced Skeeter got the wrong test results. But soon Skeeter starts to spend less time with Doug and more time thinking about going to college, and Doug thinks he's lost his best friend.

All of Doug's friends have cool bikes, but Doug hates his--until he discovers that someone has stolen it. He thinks about who could have taken it, and wonders if one of his friends is a theif.

Doug and Judy get into a fight and blow their big chance to stay alone in the house while their parents are on vacation. Instead, they're cursed with the very, very strict baby-sitter, Mrs. Stintson.

An envelope of money falls from a speeding car and Doug finds it with a huge fortune in it. Doug hands it in to the police and everyone makes fun of him for doing it. After no one claims the money, the police tell Doug he can keep the money. When Doug discovers who the real owner is, he must choose between what's legal and what he knows is right.

Theda invites Judy's new boyfriend over for dinner, but Judy is embarrassed by her boring family, especially Doug. So she decides to ""spruce"" things up around the house.

Doug is having his first house party, and he is very nervous about it--especially when he sees how his parents are planning for it. But when Roger suggests to play Truth or Dare, Doug hopes it makes his party better.

Skeeter exaggerates about how Doug can ride on a horse and Doug lets his friends believe the lie. But then Roger challenges Doug to show them, and Patti suggests they all go to a dude ranch to settle the argument. Since Doug can't ride a horse very well, he's nervous about going to the ranch.

Doug and his friends are getting ready for the end of sixth grade and are graduating from Bluffington School. Doug feels a bit sad about leaving so he tries to find Principal Buttsavitch to talk to him. But when he finds out that Roger is as reluctant to leave the school as he is, Doug convinces Roger (and himself) that the new school will be great.

As the summer begins, the Funnies plan to drive across the country to visit the Great Painted Gorge. Phil is committed to keeping to a schedule, but Doug and Judy convince him to stop at several tourist traps along the way. The family isn't having any fun on the trip, until they finally reach the stop that makes it all worthwhile.