The Devil himself visits Jim to remind him of the deal they made years ago, when Jim promised to give away his fifth child if the Devil helped him win over Cheryl.
Jim anxiously awaits for the moment when Cheryl is off bedrest so she'd take over all the chores, but Dana urges him to let Cheryl rest until she goes into labor. After meeting Cheryl's gynecologist, Jim learns that Cheryl was already allowed to be more active, but she didn't tell him.
Cheryl insists on playing a game that she somehow always wins, but Dana is aware of the fact that Cheryl is cheating.
Dana puts Andy under hypnosis to learn why all of his relationships don't last longer than six weeks. Upon learning that it's due to Andy's low self-esteem, Dana decides to boost up Andy's confidence, but she ends up making things worse when Andy starts flirting with other women while on a date with Emily.
Andy finally meets the perfect girl, but things get rough when he lets Jim babysit the woman's daughters, who then end up missing while Andy is having dinner with Emily.
Jim makes a rule he believes to be the perfect cure for children's fights, but when he enters a discussion with Andy, the both end up on the same "tribunal system," fighting to prove who's right.
Realizing that Andy didn't use the gift certificate that Jim gave him for his birthday, Jim decides to use the certificate to treat himself with a nice meal, but soon Jim finds himself in an uncomfortable situation when Andy remembers the certificate and decides to invite Jim to join him for a meal.
Jim finds a way to use Cheryl's forgetfulness (a.k.a. "the pregnancy brain") to his advantage by trying to convince her that it was her idea to turn the basement into a media room instead of a room for Ruby and Gracie.
Jim is forced organize a doll-themed party for Gracie while Cheryl is on bed rest, but when Gracie admits that the only reason she agreed to the party was because she wanted to please her mother, Jim decides to turn the party into something totally else.
Without consulting with Cheryl, Jim transforms the garage into a cigar lounge and donates the kids' old clothes and furniture to charity. When Cheryl informs Jim that she is pregnant with twins, he is forced to retrieve all the stuff that he gave away, and has to deal with the fact that he is going to be a father of five.
When Cheryl returns home for a visit the kids end up occupying her time, so Jim decides to prepare a special date with her at the airport lounge, only to end up mistakenly arrested.
When Ruby and Gracie can't seem to stop fighting, Jim is "forced" to read their diaries to determine the cause, only to realize that he needs to give out delicate motherly advice to them, while Cheryl is still away.
While Cheryl is still out of town, Jim is having hard time dealing with Ruby's girl problems, so he assigns Dana to help her. However, when Dana tells Ruby to go out on a date with an older guy, Jim if forced to intervene, as he, Dana and Andy end up following Ruby to her date.
While Cheryl is out of town to take care of her mother, Jim has to take care of their kids, and he receives sympathy from a neighborhood mom. Soon, other moms start helping Jim, and he tells each one that she's the only help in the house.
Cheryl and Jim have an evening at home without the kids and decide to stay in and just have dessert for dinner. But Jim's choice of pastries causes a spat which morphs into an all-out food fight. The next day they laugh off the night's argument; Jim is thrilled that they don't seem to have to talk things out. But then Andy, who's out for revenge on Jim for coaxing his kids to play pranks on him, counsels Cheryl to really dissect and analyze her marital arguments.
When Cheryl takes a greater interest in general safety and health, Jim feels stifled by her new rules and regulations. Just after Cheryl forces Jim to wear an I.D. badge during his morning jog, Jim is head-butted by a bull on a side road. While Cheryl learns that one can't anticipate every danger out there, Jim realizes that he's willing to do whatever it takes to make his family feel secure.
Cheryl feels down when she can't use her sexuality to get a dinner table at a restaurant, so Jim tries to cheer her up by writing letter as a 'water delivery guy', but his plan soon makes Jim doubt if Cheryl is attracted to him or the delivery guy.
Crazed about the fact that Cheryl joined a dinner party club, Jim insults the very creator of women, God, who then gives Jim the power to try to do a better job, but Jim ends up making women behave like Jim would. Also, when Andy tries to make guys more like women, he turns himself and Jim into oversensitive girly guys.
