Doug is excited about going to his first school costume dance, and possibly having the opportunity to dance with his dream girl, Patti. But Doug's excitement soon fades when Roger reminds him that he has no dancing talent, so Doug goes to Skeeter for dancing tips.

Patti is rejected from the school baseball team by Coach Spitz, only because she's a girl. She then organizes her own team with the other kids who have been rejected, and challenges Coach Spitz to a game.

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.

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.

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.

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.

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.

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.

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.