Conheça Jim e toda a sua família e que apesar de ser um bonachão e ser dono de um coração pra lá de mole, ele tem um outro lado… ele é o líder de uma banda de blues mostrando assim, o seu lado Bad Boy.

Jim e Cheryl planejam uma escapada romântica para as Bahamas e parece que tudo está perfeito. No entanto, no último minuto, Dana não pode mais cuidar das crianças. No meio tempo, Andy se torna um pouco obcecado em fazer a casa da árvore perfeita para Grace e Ruby.

O gato de Cheryl de 15 anos morre no mesmo dia em que Jim tem ingressos para o jogo de futebol.

Como de costume, Jim pede a Dana para escolher seu presente de aniversário para Cheryl, uma artimanha revelada quando ele questiona o preço.

É Halloween, e Cheryl põe Gracie de castigo, proibindo-a de pedir doces nas casas. No entanto, não querendo que sua filha perca a diversão e os doces, Jim sai escondido com ela. Enquanto isso, Andy se convence de que ele está sendo perseguido por uma ex-namorada maluca.

Jim junta Dana com Nick - um cara tão perfeito que até Cheryl fica encantada por ele, o que deixa Jim enciumado

When Andy decides Dana is responsible for his inferiority complex, he asks her to join him in his therapy - but she falls for his therapist. Jim and Cheryl disagree about letting the kids to have their own TV; Jim admits to riding his motorcycle, breaking a promise he'd made to Cheryl earlier; and Ruby innocently divulges a secret of Cheryl's, exposing a broken promise of hers to Jim.

Jim está com sorte no boliche no dia de Ação de Graças e não quer parar de jogar, embora Cheryl e seus convidados o esperem ansiosamente para começar a jantar.

Andy has a new girlfriend, and Cheryl wants Jim to treat her nicely because not only is she Andy's first girlfriend sine Carrie, but also Ruby's piano teacher. During dinner, Alicia tells Jim she's a vegetarian, and not only that, but also a Peckers fan – a big insult to Jim. Alicia and Andy break up and get back together, but she keeps turning down invitations to have dinner at Jim and Cheryl's. The reason? She doesn't like being around Cheryl. Jim rubs it on her face until Cheryl confronts Alicia, who reveals it's only because she thinks Cheryl's too perfect.

Cheryl's mother is coming to visit them for Christmas and wants to stay at their house. Jim and Cheryl, however, prefer that she stayed at a hotel but don't know how to bring it up without insulting Maggie. After Jim tells Maggie that Cheryl wants her in a hotel, Maggie gives her grandma's pearl necklace to Dana. Cheryl's upset and goes to the airport to ask her mother' forgiveness, where she learns Dana only got the necklace because she doesn't have anyone in her life like Cheryl has Jim. Meanwhile, the girls think Andy is Santa.

Cheryl leaves Jim in charge of their kids and some other kids who were there to play with the girls during a Bears game. The next day, one of the kids mom calls Cheryl saying her daughter dame home repeating a swearing she heard from Jim. Cheryl apologizes for him and Jim is insulted that she always automatically takes the other person's side. Cheryl apologizes, and not too later Grace repeats the exact same word. Jim decides to teach her not to repeat it by making her say it non stop until she can't say it again. It works. 5 days later, at Ruby's ballet presentation, she slips, falls and says the word, unmasking Jim's guilt.

Jim and Cheryl agree to let Ruby model for a print ad as a one-time thing, but when the photographer calls her a natural, Jim gets Ruby an agent.

Cheryl decides to go behind Jim's back and loan Andy $1,000 for a downpayment on a new condo.

When Cheryl has a revealing photo of herself taken as a Valentine gift to Jim, he proudly shows it to all his friends.

When Cheryl reminds Jim that she beat him at racquetball years ago, he claims he was only letting her win to gain her affections, so Cheryl challenges him to a no-holds-barred re-match.

While out for dinner and a movie, Jim loses a parking spot, and later loses Cheryl when he can't let go of it.

It's Kyle and Andy's birthday, and Andy is feeling a little left out of his own special day. They decide to take him to a restaurant that serves a 4,5 lbs steak, and Jim offers to pay for the check because Cheryl isn't feeling equal to Dana, who's spending a lot of money on their kids. On the table, Dana says she doesn't mind paying the check because she makes more money than Jim, which enfuriates him. He buys a donkey for the girls so they can know he's the one they should go to if they want stuff (in this case, they wanted a poney, but "they'll never know the difference"), and it isn't until the donkey ruins a painting Dana bought for Kyle's room that they talk it out and settle their issues.

When the new DVD player breaks, Jim must find the receipt in order to exchange it. He can't find it anywhere and blames Cheryl of losing it. She says he was the one who lost it, and in order to "win" the fight, Jim buys another DVD player and tells Cheryl he exchanged the broken one. Later, Dana shows up with the receipt, in which Cheryl wrote her a recipe, and Cheryl - after realizing it was her fault after all - burns it. They get into a fight but soon decide to drop the point scoring and just be happy again.

Jim has a run-in with an old friend from his wild and crazy days who is now a cop. Jim sets out to prove he's not an 'old married guy' by staying out all night and partying. Unfortunately, this has bad consequences for both of them...

Jim agrees to take the girls for the day while Cheryl and Dana go to a doctor's appointment. At the park, Jim leaves the girls with another mom and goes to the movies... where he's busted by Cheryl. Things go from bad to worse when he tries to retrieve the kids and can't remember who he left them with.

Jim plans a surprise party for Cheryl's birthday, but gets angry and cancels it when Dana spills the beans. To make it up to him, Cheryl plans a party for him... but he's too busy bowling to show up.