Jimmy and Donna prepare for the birth of their baby. Having been told that it's a girl, plans are under way for pink blankets and butterflies. When the day finally arrives, they get the surprise of their life -- it's a boy!
Jimmy gets caught with his hand in the cookie jar when Donna catches him looking at a girlie magazine just after she's given birth to their son. To make matters worse, Jimmy foolishly enlists Gene's help with his lame defense that it's a weakness that's inborn in men. Meanwhile, Donna tries to explain to Jimmy why he really doesn't have a say in what they name their child.
Jimmy takes a liking to Bonnie's new boyfriend, Eric. It doesn't hurt that Eric's parents own the most prestigious country club in the area, Sherwood Hills. Jimmy, seeing the possibilities here, gets close to Eric so he can play golf at the club. However, after much unwarranted advice from dear old Jimmy, Eric and Bonnie break-up, only to reconcile, with the stipulation that Jimmy and Eric can't be friends and he definitely cannot play golf at the club. Donna is finally ready for some intimacy with Jimmy after having the baby. But once again, Jimmy lands in hot water by making some ill-fated comments about women. Donna refuses to give in and a competition starts to see who will give in first.
Besieged by constant interruptions, Jimmy institutes a rule that he not be bothered from 9:00 to 5:00. To set a good example, he even stands by the edict when the family is invited out on a yacht by a new beau of Peaches. But when he's finished working by 10:30 AM, and there's nothing left to do except build a wooden boy named ""Woody"" to keep him company, he realizes why he decided to work from home in the first place.
Jimmy has discovered the newest way of controlling the women in his life and getting everything he wants by crying. Through Gene's ""coaching,"" Jimmy sets out to soften the ladies up by showing his sensitive and emotional side. It works like a charm, until the ladies catch on and turn the tables on Jimmy and give him a taste of his own medicine.
Jimmy finally receives a settlement check from an accident that totaled his car and left him in a neck brace. Having an extra $20,000 leaves the whole family dreaming about what they could spend it on. Disregarding what the kids or Donna would want, Jimmy decides to join the posh country club instead, thinking the whole family could enjoy the high class amenities. However, once the family gets there, they realize there are a lot of rules that come with the place. Rules they don't like.
Jimmy feels that he's losing his sex appeal with Donna and sets out to gain it back. His antics lead him to a possible compromising position with a woman at a hotel, but it goes nowhere. Jimmy doesn't want to have an affair, he just wants Donna to think he's having one. He sets out to prove to Donna that some women still find him irresistable. Meanwhile, new grandmothers Peaches and Mitzi, are reaching their most competitive edge as they both try to be the first to make new baby Chester smile.
After winning the lottery and $25,000, Mitzi decides to spend the money on an amazing cruise to the Greek Islands. That is until she meets resident gigolo, Don Rio Sepulveda. Don Rio gets a whiff of the small fortune Mitzi has won and pours on the charm to get in good with her. For the first time in a long time, Mitzi feels the excitement and passion that has long since been gone from her life. But Jimmy is suspicious and sets out to find the true intentions of Senor Sepulveda.
A spat between Wendy and a young boy leads to an altercation between her mom and his---and a showdown between the dads. Wendy has her first encounter with a bully while at the park playing. She leaves behind her collector cards and when she goes back to get them, they're missing, and she's convinced that Timmy, the bully, took them. Jimmy offers to go back to the park with Wendy to ""rough him up"" a little but Donna decides to handle it in her calm manner. While at the park confronting the culprit, Donna ends up losing her cool with the kid and his mother later shows up at the house to ""address"" Donna. The rage continues and Jimmy steps in, offering to meet with the father and ""do whatever he has to do"" to get those cards back. When the gentlemen meet, we discover that neither is cut out to fight anyone.
It's Thanksgiving time and Donna is busy preparing all ""the fixin's"" for this year's dinner while Jimmy handles bird duty. Taking it ultra-seriously, he sets out to find the best bird - the MacAdoo! However, unexpectedly, Donna's sister Delilah shows up in town and changes everyone's plans by taking over Thanksgiving. Donna is once again reminded about the many things that drive her crazy about her domineering, snobbish and overwhelming sister.
A bounced check prompts Jimmy to put the family on a budget -- which, amazingly, has room for his new set of golf clubs.
In an effort to surprise the family with a spectacular Christmas gift, Jimmy buys a Hawaiin vacation for five from a friend who can no longer use the tickets. Thinking he's going to score big points with the family, he is shocked when their reactions to this luxurious gift are less than stellar. Once the family actually gets to the airport, one crisis after another prevents them from even getting off the ground, let alone to the Aloha State for the holidays.
When Gene's new hot, young girlfriend makes waves in a hot tub by taking off her top, while Donna feels more comfortable taking a dip dressed in her robe, Donna fears she's lost her ""whoa"" and has become a ""hmmm."" After Jimmy tells Donna that she's not as wild as she used to be, Donna throws caution -- and her clothes -- to the wind to prove to Jimmy that she can still be young and impetuous.
Wendy is suspended from school for three days for ""sexual harassment"" after she kisses a boy without his permission. Outraged at the absurdity of Wendy's suspension, Jimmy decides it's a chance to teach Wendy how to take a stand. But when he arrives in student court where students are the judge and jury, and a pint-sized ""prosecutor"" is out for Jimmy's blood, Jimmy realizes he's going to have to come up with a darn good defense
Donna and Jimmy's doctor/friend, Ben Carlson, and his wife Sarah are heading for divorce. Jimmy and Donna take sides and the battle begins. Peaches exposes young Wendy to make-up for the first time and Donna is not happy about it. Gene finds himself having a stroke of good luck at the car lot by selling Jaguars by the droves to bitter, soon-to-be ex-wives of really rich men. Peaches opens up her house to host an Alcoholics Anonymous party.
Jimmy lands a new -- and very lucrative -- job at a company that sells furniture on the Internet. The rest of the family is convinced that this is their ticket to wealth, and they immediately begin making out shopping lists for cars, houses and horses. Surprise! Jimmy learns the hard way that he was most happy working at home, working hard and making less money…as long as he could spend more time with his family.
When Mitzi's flamboyant sister Lou comes to town, everyone is thrilled to see her -- except Mitzi. Jimmy tells his family about how his childhood was intolerable until he'd see his exciting, risque Aunt Lou for two weeks each year, and Mitzi is reminded about how her colorful sister always hogged the spotlight -- and her son. Now, Aunt Lou has offered to take Bonnie on a shopping spree to New York City, ruining Mitzi's plan to spend time with Bonnie. Thinking she is supposed to meet Lou at her friend Terry's loft, Mitzi finds herself the center of attention at ladies night out - Terry holds weekly support groups for a Transgendered support group. The ""girls"" show Mitzi more than just a better way to apply mascara, soon she sticks up for herself and confronts years of sibling rivalry.
Jimmy's being lazy when it comes to healthy living and the ladies won't stand for it. Golf isn't exactly what Donna has in mind when she suggests that Jimmy start an exercise routine. Gene is quick to the defense-especially when Jimmy inherits a set of clubs from his buddy Stan whom recently (and unexpectedly) past away. When Stan's widow uses a full body make-over to cure the grief, Gene is hot on her trail. However, it doesn't take long for harsh reality to manifest into Jimmy's worst nightmare. Now more awake to the matter at hand, he has to set things straight with Donna to assure that she will never follow in the fake footsteps of Stan's wife. His weapon: A personal home video collection not available in stores…to say the least.
Money can't buy you love -- that's what Jimmy thinks until Donna's former boyfriend, now a millionaire, offers him $10 million for his wife. Meanwhile, Bonnie and Mitzi study for their driver's exams.
Donna and Jimmy declare war when their new neighbors try to ""out nice"" them. Donna and Jimmy welcome their new neighbors with a token gift basket, and they're happy to find that Shirl and Harve Henderson seem to be very nice people. But when Shirl comes over to thank the Stiles with a much bigger basket filled with very expensive gifts, Donna cries foul and decides her next door neighbors may be nice -- but with an agenda.
Donna refuses to let Mitzi baby-sit anymore; Gene uses Chester to lure women.
Mitzi's old flame returns to town and heats up some sibling rivalry between Mitzi and her sister Lou and offers Jimmy pointers on how to be romantic. Meanwhile, Wendy has her first date.
Waking up on the morning of their 10th anniversary, Jimmy and Donna find themselves revisiting the same argument they've had for the past ten years. It seems that on their wedding day, Jimmy ""wimped out"" and didn't write his own wedding vows as they had planned on doing together. His reason being that he thought he would embarrass himself by starting to cry during the ceremony. When Donna doesn't believe him, Jimmy shows her the 10-year-old vows that he kept all these years and before you know it, no one seems to be arguing anymore. Meanwhile, downstairs, the girls work to make their annual anniversary breakfast for their parents as special as possible, despite needing a fire extinguisher along the way!
Jimmy starts his new career as a full-fledge building contractor. His first client: game show host Alex Trebek. With the help of his architect partner, Jimmy learns that there is a special way of dealing with celebrity clientel. Jimmy also coaches Gene in the art of making moves on women. It seems Gene has it together when it comes to approaching people in the Jaguar showroom where he works, but with women, he hasn't got a clue. However, after selling a beautiful woman a new car, Gene musters up the courage to ask her out. Meanwhile, Wendy gets a dog from the pound that is anything but a ""standard"" poodle.
Jimmy and Donna are in a continual amorous mood and at every turn, someone manages to walk in on them while they're ""getting close."" Afraid they've scarred Wendy for good from this experience, they attempt to broach the subject of the birds and the bees but realize that she's still too young to even care to hear it. Jimmy makes his first appearance on-site as the building contractor at Alex Trebek's house. It seems our celebrity client has some pretty outrageous ideas for his home and it's up to Jimmy and Sabrina, his architect, to try and make them happen. A woman named Mel Hanlon, who used to live in what is now Jimmy and Donna's house and who also happens to be an ex-therapist, arrives on Donna's doorstep in the hopes of taking a nostalgic look at her old home. A friendship strikes up between the two and it appears we may see Mel more in the future.
Donna and Jimmy make a wager to see who can collect the most phone numbers at a speed-dating place where singles rotate around tables trying to get to know each other in five minutes.
Having not had a sit down dinner with the entire family in quite a long while has gotten to both Donna and Jimmy. They decide to set up a new rule, which is that the family will start eating dinner together more often. No more nights out with friends, no more excuses for having other things to do. However, one thing after another keeps this from happening and the evening keeps getting pushed back. Gene, who has been pining after new-found ""gal friend"" Terry, although she has a boyfriend, gets his one wish when Terry's relationship goes on the brink and she comes running after Gene. In an effort not to move too quickly, Gene finds himself having to go to great lengths to keep at a safe distance from Terry.
Jimmy is crushed when Bonnie decides to break up with Mitchell after developing a crush on the hunky guy who delivers their water. Meanwhile, despite Jimmy's advice, Gene continues to stalk Terry.
Jimmy and Donna learn that Bonnie, despite failing her driver's test three times, has been borrowing their car at night; Wendy finds out she was born out of wedlock.
Jimmy fears that Chester will grow up to be gay because of all the females in the house; Gene learns Terry still isn't over Elliott.