Pickles decides to quit smoking, but she replaces one addiction with another when she channels her nervous energy into becoming a reckless thrill-seeker. Her decision comes much to the dismay of Bob, who worries about her safety, and Milo, who resents her unseating him as the crazy one in the family.

Milo runs for school president against Debbie Klimer, leader of the snobby Debbies, and he loses -- but then his opponent suffers a freak accident. The Klimer family fakes young Debbie's death while she goes under the plastic surgeon's knife, but the operation is less than successful and Debbie returns looking like The Phantom of the Opera. Shunned by her upscale family and friends, The Oblong clan and the valley kids take in the reject Debbie as one of their own. But when Debbie's cheerfulness starts getting on everyone's nerves, the valley kids turn to the freakish school nurse to get Debbie back with the in-crowd.

When Bob's coworker, James, orders a mail-order-bride on eBay, he throws a bachelor party at a strip club -- which Bob mistakes for a "colonial themed steakhouse." Bob accidentally ends up on stage and a stripper steps on his "family jewels." He goes to the doctor, who says he can't have sex for two weeks.

When Pickles is convicted of being an unfit mother, her punishment is having to do community service -- as the leader of a Girl-Scout-like group called The Little Amazons. When it's brought to her attention that her group is short one girl, Pickles comes up with a solution -- putting Milo in drag.

Everyone is excited about Dump Day -- the day when the Valley people get to loot the stuff the Hill people have thrown away.

Biff and Chip finally get their driver's license -- and end up smashing Bob's car. To make it up to their Dad, the male siblings chip in to buy a new car at an auction.

Milo soon grows attached to a stray Scottie dog the Oblongs take in, but the pet brings out the animal in the hyperactive boy, and the family gives the pooch away to Bob's boss, George, thinking he'll have a good home. But when his new owners soon tire of him, Scottie finds himself in an animal testing lab, sniffing perfume with narcoleptic side effects. So the Oblongs set out to rescue Scottie before it's too late.

After a disturbance in the Hills is blamed on Valley kids, the Valley's mayor appoints a child-services czar to improve parenting skills. Elsewhere, Milo learns that his freaky friend Helga has been abandoned by her parents and he is forced to spend every evening with his lonely pal. But Bob and Pickles suspect their son's late-night antics may be because he is on drugs... more than his numerous prescribed pharmaceuticals, that is. And Chip and Biff walk in on their parents at the wrong time. . .and end up having to scrub their corneas.

To keep dry in the rain, Pickles puts a bucket on Milo's head and sends him off to school. Funzie, the cool guy, thinks Milo's bucket is hip, so the next day, everyone's wearing a bucket on their heads. Milo finds himself running with the in-crowd, so he sets out to launch a strange new line of apparel -- with disastrous results.

Milo and his friends crash a party thrown for the Mayor's daughter, Debbie Bledsoe, and they cause the Debbie's new locket to be tossed into the sewer. The zaftig Helga goes after the gift and gets lodged in the pipe, plugging it up like a human cork. The hill people and rescuers work feverishly to rescue... the locket, and leave Helga blocking the main water line -- just one flush away from the great beyond. Helga causes a disruption in the water supply to valley, but the hill people pay no attention -- until their water is cut off too.

After learning that one more expense and the family will lose their medical coverage, Bob futilely urges the family to be extra careful. Milo finally manages to get himself enrolled in public school, where he meets and falls in love with a very unique student.

Bob fears his career is going nowhere. That is, until marketing genius Milo's sales take off for his new energy drink, "Manic," which improves Bob's co-workers' productivity. But the real secret of his success is found out when Bob's company anoints Milo as their new CEO.

A freak accident at a Globicide-owned amusement park leaves Bob unable to use his mouth. Out of compassion (and at the advice of their lawyers), the people at Globicide build him a robotic suit with limbs that he can use to perform his duties.