Dave puts the kids on a strict allowance, since they're always asking him for money. Vicky supports him on this... that is, until she, too, is put on a budget and is unable to buy the Prada boots she's always wanted. Meanwhile, after spending all his allowance money on the first day at Medieval Times, Larry asks Mike to loan him some money. And, in order to earn some extra money, Hillary starts an escort service for the nerdy boys at school.

When Larry wears Dave's jacket to school by mistake, he ends up getting suspended for 30 days by Principal Fink for finding pot in it. This leads to Dave and Vicky trying to get him enrolled in a parochial school with the same priest who Mike thinks is hitting on him.

Vicky's mom Betty and her boyfriend Sid announce their engagement and upcoming wedding in St. Martin and invite the entire family to join them. But when Sid goes too far with a stripper, Dave wonders whether or not to tell Betty and risk losing the free trip. Meanwhile, Kenny goes on a date with an ex-boyfriend of Hillary's, so Dave has an awkward conversation with him about gay safe-sex, while Hillary worries she may have a knack for turning men gay.

Because of failing gym class, Hillary risks not graduating high school. Feeling that their nest is emptying a little bit, Dave and Vicky feel the need to keep it that way, resulting in both of them agreeing to have no more children and taking steps to prevent that from happening. But in the end, Hillary graduates and a shock for Dave and Vicky unfolds.

When Larry decides to run for president, Dave is supportive of his son's interest in leadership, until he learns that Larry is actually running for president of the Chess Club. Dave makes a strategic move to prevent Larry from becoming the biggest geek in school. Meanwhile, Hillary thinks she's going to become the next pop star, and after finding an empty condom wrapper in Mike's pants, Dave and Vicki face the dreaded sex talk.

Dave and Vicky decide to give Hillary the car she wants as long as she agrees to sign a contract so they can completely control her life. She reluctantly signs, but Dave and Vicky realize they may have gone too far with the restrictions. Meanwhile, Larry goes against the "bros before hos" code and dates Mike's ex-girlfriend, Heidi.

When it's revealed that Kenny and his date will be attending the school's Sadie Hawkins dance, he and his date are both banned from the event for not keeping with its traditions. This prompts an outraged Larry to lead protest against the discrimination, while Dave goes to the school to argue the case. Meanwhile, once Principal Fink discovers that Kenny's been living with the Golds, he tells Dave that he must inform Child Services so that Kenny can be put in foster care, unless Dave can convince Kenny's parents to let him come home.

Dave is tired of Larry and Mike's constant fighting and suggests that Mike try harder to have a relationship with his brother. Much to Dave's disappointment, Mike actually prefers hanging out with Larry to practicing for basketball tryouts, and worries that Larry's nerdy ways are starting to rub off on him. Meanwhile, Hillary sets out to prove she's more than just a pretty face by trying to get a blind guy interested in dating her.

Kenny confronts Dave after hearing that he thinks he's gay, and ends up coming out of the closet to him. Dave suggests to him that he tell his parents, but when Kenny tells them, they kick him out of the house. Meanwhile, Hillary goes on a date with a blind guy she met at the coffeehouse, but she quickly gets tired of having to describe everything to him.

When Kenny moves into the Gold's house, Vicky sets out to re-decorate the basement for him, however, her ideas don't meet Kenny's standards, and Larry, Hillary, and Mike try to get him to stop showing them up by doing all the chores and laughing at Dave's bad jokes. Meanwhile, Dave uses Kenny's moving in to his advantage and tells everyone at work he's taken in an "orphaned gay kid" so that he'll look like a good guy and hopefully get the newly-vacant, larger office.

Due to cutbacks at work, Dave and his two co-workers quit their jobs and start their own business. Meanwhile, Hillary decides to join the Army after not receiving any college acceptance letters, and Larry refuses to get his driver's license.

Larry meets with a music executive who wants him to make a demo after hearing a song he composed for a website. After learning about this, Dave reveals that he considered himself to be the original white rapper in high school, known as The White Shadow, and offers to help Larry with the lyrics. He wants to show him the support his own father didn't show him. Meanwhile, tired of being mistaken for an Olsen twin, Mike decides to bulk up, and Hillary questions Taye's motives when he tells her he loves her.

Hillary dupes her parents when she introduces them to a classmate she’s pretending to date, but ends up going out with a much older guy. Meanwhile, Larry gets addicted to Vicky’s nicotine gum and Dave catches Vicky smoking.

Fearing they're in a rut, Vicky tries to take Dave to a wine appreciation course, but he refuses, and later makes fun of her because she goes without him. Meanwhile, Dave assumes Larry is serving his new, older "ladyfriend" more than just the gourmet meals he prepares for her, and is offended that he isn't mentioned in Hillary's video blog.

Larry reveals to his parents that he suffers from Social Anxiety Disorder, so Dave and Vicky try to put him on medication, but Larry refuses and accuses them of wanting to change who he is. Meanwhile, Dave is convinced that Hillary intends to lose her virginity on prom night, so Vicky ends up giving her the "sex talk."

As school starts up again, Dave is excited that the kids will be out of the house until he and Vicki realize that all of them have their own agendas. Mike questions his current romantic relationship, which upsets Dave because the girl involved is the daughter of Dave's new best friend. But when Dave meddles in Mike's life for the sake of his "man-crush" on the girl's father, he does unexpected damage. Meanwhile, Hillary changes her study habits after catching a glimpse of her future, and Larry reinvents himself for the new school year.

Kenny's dad, Achmed, pulls up the rose bushes between his home and Dave and Vicky's, believing the property is his after an assessment. When Dave and Vicky disagree, the two families declare war on each other, putting Larry and Kenny in the middle. Meanwhile, Hillary jokingly tells Dave to choose her next boyfriend since he's never happy with the boys she picks. Dave meets a boy who reminds him of himself, and against her better judgment, Hillary agrees to go out with him. Mike goes through a nude phase.

Dave starts to put pressure on Hillary for her to do well on her college admissions interview by setting up mock interviews, which only makes her even more nervous. Meanwhile, Vicky organizes a movie night for the family, and they end up watching Al Gore's An Inconvenient Truth. Finding the film very profound, Dave forces the entire familiy to live in an eco-friendly existence, but takes things too far.

Dave thinks he sees Hillary in a "Girls Gone Crazy" video, however, he's relieved when it turns out he's mistaken. But he is completely freaked at being turned on by girls Hillary's age, though. So he turns to Vicky for inspiration after he throws out all of his "visual aids," and it begins to tire her out. Meanwhile, an edited version of the movie "Goodfellas" inspires Larry to replace swear words with the word "love," and Hillary prevents Mike from taking drugs by passing PMS medication off as mood enhancers.

When Kenny's dad cancels on taking the boys to a comic book convention, Larry asks Dave to take them instead. At first, Dave refuses, but after hearing Larry call him a hero, he quickly decides to be a good father and take the boys. But when his fatherly duties go beyond simply dropping them off, Dave is pushed to the limit when it means missing the Jets football game and pretending he's a comic book geek. Back at home, Vicky introduces Mike to coffee and Hillary wants to have a sleepover with a guy.

Dave accuses an incensed Hillary of cheating on her SATs after she gets a surprisingly high score. Meanwhile, Vicky and Dave meet a couple who may be interested in more than friendship, and Dave asks Larry to take a client's daughter out on a date, only to find out that she isn't an ideal match for him.

After a car accident, Dave and Vicky decide to look over their living wills again, and ask their friends Jeff and Mindy to become their children's legal guardians should anything happen to them. They can't accept due to already doing the same thing for their other friends, so disagreements between Dave and Vicky start up, causing a huge fight. Larry thinks they may be getting a divorce, so he, Mike, and Hillary come up with a plan to get them back together.