Janet's old high school boyfriend Joey Russo, a famous writer, comes back to town and Janet invites him over to have dinner with the family. However, things don't go well when tension builds between Marshall and Joey and Joey proves to not be too helpful when he offers Clarissa advice on a paper she's writing.

After Sam's mom Debbie arrives in town, she announces that she's going to take Sam back to Seattle with her. Clarissa and Sam remember all the great times they've had before they have to say goodbye.

Clarissa is chosen to represent her school at a poetry banquet after her computer helps her write a strange but well-loved poem.

Clarissa and Ferguson are left home for the night and try to scare each other with a huge war of spooky pranks. However, they both end up being scared out of their wits when someone tries to come inside the house.

Clarissa learns a thing or two about money and responsibility when she lands several part-time jobs and tries to keep up with all of them.

After Janet asks the family to participate in Volunteer Day at the Chidren's museum, Clarissa tries to figure out a way to escape her duty of helping out.

Clarissa tries to ruin Ferguson's new romance with Fiona by giving him lots of bad advice. But her plan backfires when numerous girls from school start to go crazy for him.

As Marshall's birthday arrives, he loses interest in everything and decides to sell the house and move the entire family to Mango Island. Everyone goes along with the idea until Marshall has a couple interested in buying come look at the house and they realize just how serious he is.

Marshall bets his neighbour that a Darling can make the varsity football team. But Ferguson realizes that the only way he's going to make it is by marketing himself as the Smallest Student Football Player. Clarissa runs Ferguson ragged during special 'training' for football try-outs.

After Clarissa accidentally walks out of a clothing shop while wearing a piece of lingerie that she didn't pay for, she has nightmares about being a hunted criminal. When Clarissa doesn't want to tell Sam what's bothering her, it causes tension in their friendship.

The Darling's are in for a surprise when Marshall's parents come to visit and have completely changed. Clarissa also must figure out how to be the DJ at her grandparent's anniversary party and go to a Pearl Jam concert with Sam in the same night.

After Sam sets up himself and Clarissa up on a double blind date, Clarissa starts to contemplate all the ways that the date could go bad and what her blind date Milton might be like. Meanwhile, Ferguson takes an interest in law and starts filing suits for his parents without their knowledge.