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.

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.

Dave decides to take the family to Florida to visit his parents, and because it won't cost him a dime. But he soon learns that Mike hates to fly, Vicky hates his parents, and Hillary wants to remain in town so the boy she likes won't forget her. This leaves Larry the only one actually looking forward to going on the trip, and has started a weight-loss program so he'll look good in a speedo. However, everything soon starts to go wrong when their ride to the airport is cancelled, Hillary's new nipple ring is discovered by airport security in front of an angry Vicky, and Dave is searched by security. Once they reach the condo, Dave is continously treated by his dad the same way he treats Larry and wants to return home as quickly as possible.

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.

One of Hillary's friends gets breast implants, so now, Hillary wants to get implants, too. However, both Dave and Vicky won't let her do it, as Dave tells Hillary that it's what's on the inside that matters, not appearance. His advice is then tested when he meets Larry's new, overweight, unattractive girlfriend, Marla. Now, he'll have to figure out how to tell Larry that he can do better without going against what he told Hillary earlier.

Jodi, one of Vicky’s college friends visits to reveal that she is now sober. But now Dave is afraid that Jodi will tell Vicky that they (Dave and Jodi) had sex in college.

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.

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.

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.

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.

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.

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.

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.

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.

When Vicky refuses to buy Larry Ice Capades tickets, he runs away from home hoping she'll give in so he can see Brian Boitano star as Bilbo Baggins in "The Lord of the Rings" on ice. A disbelieving Vicky holds her ground, but when she realizes Larry really did leave town, she questions her parenting skills. Meanwhile, Dave tries to support Hillary in a fight with one of her friends, but when it backfires on him, Dave and Vicky get tired of parenting and ditch the kids.

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.

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.

When Hillary and her friend Brenda are caught arriving drunk late at night, Dave and Vicky decide to ban alcohol in the house. However, this only lasts two days, as Vicky and Dave fall victims to some free alcohol with their friends and arrive home drunk themselves. As they arrive, they'll have to face Hillary and Brenda's strict parents, who are waiting for them. Meanwhile, after accidentally shooting a pigeon, Mike decides to become a vegetarian.

When Dave thinks the kids are getting away with too much, he implements a zero-tolerance, pro-spanking policy, since talking to them just isn't working. However, they all think he's bluffing and don't take him seriously. After Larry becomes the first to be spanked, he moves in with his friend, Kenny. Now, Child Protective Services is called and Dave will have to answer to them.

Dave suspects Hillary is pregnant when he finds a pregnancy test in the trash. However, he soon learns that a depressed, jobless Vicky has not been taking the pill. So, Dave insists and helps Vicky with various job opportunities, but with no results, since he is opposed to having another kid. Mike, meanwhile, becomes too lazy and buys Hillary's old book reports when she had good grades, and Larry gets himself into a spelling bee competition.

Mike asks Dave for a bar mitzvah, but he believes Mike is only in it for the party and gifts. However, Mike expresses geniune interest in Judaism after studying Hebrew, so Dave and Vicky are willing to support him and throw him a "coming-of-age" ceremony. Hillary also decides she's interested in being Jewish after Mike's attractive Hebrew tutor. Also, Larry gets the confidence he needs to ask out an attractive girl at school.

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.

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."

Dave isn't happy when Taye's family is invited over for a barbecue by Vicky, and has a hard time getting along with Taye's father, Omar. At the barbecue, Omar mistakes some of Dave's comments as racist, because he's a wealthy, African-American. However, when Vicky insists that he go apologize to him, Dave finds himself having a great time at Omar's country club. When he gets home, though, he finds out that Hillary and Taye are on the verge of breaking up.