Pepper Ann Pearson, a spunky too-cool-for-7th-grade girl, has just started middle school. It's yearbook photo day and just when Pepper Ann was thinking her life couldn't get any trashier, she gets a zit. The solution? Zit cream, but she'll have to go to Abe's Mall (or commonly called Abys Mall, as in your life will be an abysmal if you get seen there) to get this cream. At least there's an advantage, 33% discount!

Romeo and Juliet Pepper Ann tries out for a play because Craig has the lead role of Romeo. When the time comes around for the results, she's a runner-up to Cissy who's gotten the lead role of Juliet. Pepper Ann got the role of "Nurse." Meanwhile, Milo is O.D.ing on juice boxes. Finally when it's time for the play, Cissy loses her contact lense, and Pepper Ann gets the lead role, but an accident causes Craig to be replaced by a chubby Milo.

In economics class, Pepper Ann and friends get assigned partners and have to work at a job for a week. Pepper Ann has to work at Food Barn with Milo. While there Milo gets a promotion, Pepper Ann? Nothing; Milo gets praise, Pepper Ann? "Clean this up clean that up." This drives Pepper Ann wild. Meanwhile, Deiter is not showing up at his job because he's been at the Food Barn eating all the strudels.

Pepper Ann gets all excited to see her old friend "Brenda" from Cubby Camp, but to find out she's very Uncool and still acts like she did 5 years ago!

Milo, "the king of crunch," accidentally gets beaten by Pepper Ann in a Crunch Pod tournament. They then have a "who's better" fight

Seeing moose hanging out with the mall psychic, Pepper Ann gets the feeling that Moose is psychic.

Pepper Ann and friends are assigned dolls that must accompany them everywhere. Pepper Ann thinks she's irresponsible because she keeps losing her doll, and can't get it to stop crying.

Pepper Ann exploits and takes advantage of Milo's skill of being able to cut grass, and trim bushes into the shapes of various things, just to get herself some MegaBlade 3000 roller blades.

Pencil Pepper Ann wants to beat Alice Kane by building a better science project. The trophy? A giant pencil.

Pepper Ann's school gets a invited to the Sani-Paper toilet seat cover factory because no other place will allow them to come. While there she makes several observations such as; 1 large tree makes only 1 toilet seat cover. She then learns that there's much more going on than she saw.

Principal Hickey thinks that school uniforms will improve the school, so he hires P.A.'s mom to make the uniforms. Pepper Ann thinks everyone will hate her because of this, but she's wrong.

After Pepper Ann gets tickets for a sold out concert, she learns her mother knows Mick Snot from her favorite band Flaming Snot.

Pepper Ann joins the environ-mentals and tries to solve the problem that the pyramid peanut butter can presents (skunks crawl in and suffocate).

The Hazelnut Middle School Otters are back and awful as ever. However, Pepper Ann gets in the game and becomes a star. But the success goes to her head and she needs to be taught a lesson.

Milo is upset that Gwen Mezzrow has a crush on him, so Pepper Ann comes up with a genius idea - her and Milo are a couple. One lie leads to another, which leads to another...until it gets totally out of control.

Pepper Ann's dad has called, saying he has a surprise for her. Pepper Ann thinks he will come and visit her. Meanwhile, Lydia and her aunt Janny are trying to have the best Thanksgiving ever. But; the turkey burns, Ned eats all the yams, and they have to resort to Butterscotch pudding as yams. So they go to plan B and dinner is solved. Pepper Ann finds out her dad is going to visit her next week. Everyone enjoys dinner, even Milo, who was invited by Pepper Ann, who is grateful for everything.

Pepper Ann gets invited to hang out with an eighth grader named Sketch.

Milo tries to be more of a man by hanging out with guys, but the guys reject him because he's always seen hanging out with two girls. He then learns that how macho you are doesn't really matter.

Deiter is now turning 13 and he decides to have an unsupervised birthday party. This is the type of party where anything can happen, including "spin the bottle."

The otter statue was stolen, and unfortunately this is an inanimate object. Principal Hickey calls in possible suspects to hear their story of where they were at the time, and what they were doing

Nicky gets tired of caring for everyone, and decides to stop. She also decides to stop being a goodie two shoes, and be bad. Very bad. All the adults she talks to just ignore her new behavior though, this just makes her even angrier...

Pepper Ann hears about "support" in gym class, and goes on a quest to find information, and a bra. She goes to her mom to find the information part.