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George and Marsha have conflicting events. George has a high school reunion and Marsha has a convention in Atlantic City and both places have things about them that are a bit tempting, gambling for Marsha and for George it's an old flame he once had a crush on and who's eagerly fanning it now.

After a disasterous date, Kevin vows to give up women and he throws himself into his part-time job. However, one evening he meets an older woman whom he instantly becomes smitten with which leads to him losing his virginity. Later, his parents aren't exactly happy when they meet his girlfriend.

Kevin's 18th birthday is approaching and he's apprehensive for his first sexual experience. Pressure from his friends doesn't help any when they suggest he take out a girl who has a reputation for being easy. Kevin quickly finds himself in an uncomfortable situation when he takes their advice.

Fired from his job, George finally decides to go down to the unemployment office, however, George quickly finds himself the community hero, when he saves a woman from a mugger. However, the media attention leads the Owens' financial situation to become public knowledge and the they find themselves swamped with gifts from the people in the community.

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Kevin gets a ticket after he goes through a stop sign but complains that he could see the stop sign due to a tree branch being in the way. This leads Marsha to test her knowledge at law and represent Kevin in court. Meanwhile, Mr. Belvedere is after a raise and George is dead set against giving him one.

Kevin agrees to go to a Huey Lewis concert with Heather's best friend, Angela. However, this one date, ends with Angela coming down with a serious case of puppy love, much to Kevin's dismay. Meanwhile, Wesley and Mr. Belvedere camp out in the back yard.

Wesley becomes a mini-mogul when he organizes a company that goes around the neighborhood doing odd jobs. The company starts off small with just him and Miles as partners. However, when greed overwhelms Wesley, Miles splits leaving Wesley power hungry and taking advantage of his employees.

Heather and Angela are participating in an Adopt-a-Grandparent program at a retirement home and Wesley is talked into going with the prospect of squeezing some money out of and unsuspecting old person. However, Wesley makes quick friends with one woman in particular but he soon realizes she has Alzheimer's disease.

George is to become a member of The Happy Guys of Pittsburgh but on the night of the induction, which happens to be Halloween, George and Marsha discover the Happy Guys have a dark side. Meanwhile, Mr. Belvedere shows a different side after he goes wild toilet papering a house while trick or treating with Wesley.

Wesley is competing in a spelling bee at school and one of his female opponents' cozies up to him but her intentions are hardly innocent. Meanwhile, Mr. Belvedere puts the Owens family on a strict budget after their spending habits get out of hand.

Marsha gets some unexpected news that she may be pregnant which brings back the feelings she had when she became pregnant with Wesley. Not wanting another baby, Marsha voices her feelings and says out loud that she didn't want Wesley, unaware that he was standing behind her.

Heather and Angela get a job at a music store and at least Heather seems to have enough responsibility to do a good job, that is until she begins dating the captain of the football team and he just assumes it would be okay to stop by Heather's work and rip off a few things. Meanwhile, Mr. Belvedere tries to beat Wesley at gin rummy.

Heather has become convinced that she's fat and decides to try diet pills, but when Marsha discovers them, she confiscates them. Meanwhile, Marsha has been studying for an exam and a bottle of amphetamines may just be what she needs to keep her alert.

Tired of George's smug face everytime he beats him at arm wrestling, Kevin becomes to determined to beat his father and has Mr. Belvedere coach him. Meanwhile, Heather begins dating the football jock who's been ordered to take ballet class by his coach. However, when he shows little interest in her, she begins to question his sexuality and he becomes convinced he's a homosexual.

Wesley has gotten totally out of control and George and Marsha are up in arms over his constantly getting into trouble at school and at home. When George threatens to put him in military school, Wesley is sure he's just joking, but Wesley is certainly not laughing when he finds himself there.

Kevin has been looking at colleges and has even gotten some acceptance letters, however, the schools he wants to attend are too expensive for the Owens' family, so he quickly informs his family, that he just wants to get out of the nest and away from their rules. Meanwhile, Mr. Belvedere is horrified at the prospects of teaching Heather how to drive after she receives her learners' permit.

Wesley is heartbroken when his pet hamster, Inky, dies, so to cheer him up, George and Marsha buy him a dog. However, little do they know, Wesley has faked Inky's death for the sole purpose of getting the dog. Meanwhile, one bathroom in the Owens' household, has George and Marsha thinking of adding on to the house.

With George out of work and Marsha busy with law school, they have been spending little time together creating tension between the two. After a failed weekend at a marriage retreat, the decide to seperate, and George moves into an apartment.

For a charity auction at Wesley's school, Mr. Belvedere is talked into having his services auctioned off. However after his time is up, the lonely woman who bid a whopping $500 for his time, sets into motion a bizarre scheme that begins when she drugs Mr. Belvedere.