16-year-old Hillary's father, Dave, refuses to let her go out on a date with a guy older than her. So, to deceive him, she brings a new ""study buddy"" over to the house instead. At the same time, Dave and Vicky are having trouble trying to figure out how to understand their son, Larry.

Vicky decides to turn to an old, ex-boyfriend over the internet for advice about what to about her son, Larry, who insists on wearing women's clothes. While she's online, though, she discovers some of Dave's secret e-mails he's been sending to someone with the screenname ""Lonely Lady in Michigan."" Having discovered this, she decides to confront him. However, Hillary also has some problems of her own, but refuses to to tell Vicky about it.

When Dave notices how nice Hillary has been to him recently, he is certain it's because she's having sex with someone. However, Mike spies on her and confirms that Dave is actually wrong. Dave then comes to the conclusion that she's smoking his pot when he notices his stash has gone missing. As he's confronting her about it, though, he accidentally tells her that it's his, but quickly tells her that it's not really his - it belongs to Vicky's mother, Betty, that she uses for medicinal purposes.

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.

When Dave finds out that Hillary is asking Vicky about sex, he plans an unexpected family trip to prevent her from going out on a date on Saturday night. Meanwhile, Kenny can't accept the fact that Larry has a new girlfriend, so he tries to break them up.

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.

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 becomes upset with Larry because of his lack of interest in masculine activities, and his lead role in the ""Annie Get Your Gun"" play at his high school. Things get worse for Larry when his parents see him kissing what they think is a guy, which convinces them that Larry is, in fact, gay. Meanwhile, Hillary has to deal with her new image at school after she hits another girl and gets dumped by Taye.

Grandma Betty comes over with her new boyfriend for dinner with the family. However, soon, Dave finds out that she is spending a lot of money on him. Fearing that he'll lose his future inheritance, Dave accuses Grandma Betty's boyfriend of being a gigolo in order to break them up. Meanwhile, Vicky and Dave devise a plan to break up Hillary and Keith by showing Hillary how hard it is to raise a baby. Then, when Larry shows interest in baseball cards, Dave encourages him... until he learns that Larry is using the information to sell his cards on eBay.

Vicky becomes inspired to be more ambitious by Mike when he scores high on a test, with the option of taking the honors class. So, she decides to return to her fashion-executive lifestyle, which will mean an increased salary. Dave supports her all the way until he soon learns she's too busy to do the household duties, leaving him to do all the chores. Larry, meanwhile, ends up taking too much credit after submitting Kenny's poem as his own.

The family struggles to adjust to Vicky's new job, which leaves her with less hours to be at home and more hours working. Dave and Larry continue to have tough time trying to do the things Vicky normally does. Dave's temper doesn't help and makes matters worse when Mike and Hillary end up in trouble. Meanwhile, the changes around the office force Vicky to think twice about her decision.

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.

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.

Dave and Vicky attempt to cheer Mike up when they are convinced he's depressed after find a note in his room. Mike goes along with them and decides to milk the situation for all its worth... until he's taken to a therapist and is forced to tell the truth. Due to all the attention Mike is receiving, Larry becomes very upset. Meanwhile, Hillary takes a sexual experience survey for a class at school.

Dave has to deal with mood swings and PMS when Vicky and Hillary's menstrual cycles start in full swing. So, when a reluctant Dave has to take Hillary to the gynecologist's office, he soon discovers that Dr. Vogel is his old best friend, who happened to be a ladies' man in high school. This leads to the doctor's professional relationship with the family getting personal since Dave doesn't believe he's changed his ways. Meanwhile, Larry tries to do whatever it takes to gain the respect of Mike when he calls him a nobody.

Dave thinks he's still a catch for the ladies when he gets hit on by an attractive saleswoman at work. But he soon learns that she was only checking him out for her mother. Meanwhile, Vicky attracts guys of all ages when she goes to Mike's class for Career Day. And back home, Hillary gets attracted to Kenny's sensitive side.

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.

When Hillary sprains her ankle skiing and lands in the emergency room, a furious Dave becomes even angrier when he realizes Vicky gave her approval for the ski trip without his consent. But when they arrive at the hospital and learn that Hillary lied to the both of them, their argument turns into an all-out war. Meanwhile, Larry awaits a phone call from a girl and Mike takes advantage of the situation to get an older woman.

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 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.