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 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.

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.

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.

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.

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.

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 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.

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.

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.

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 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.

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.

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.

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.

Thinking that Hillary will be grateful, Dave takes the blame when she gets pulled over for reckless driving while she's taking driving lessons. However, Hillary isn't grateful at all when this leads Dave to be arrested for DUI and goes to court to try and settle things. Vicky, meanwhile, forgets to register Larry for Shakespeare camp, while Dave and Mike take up online poker.

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.

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.