When Jim chokes on a shrimp puff, he dies and arrives at Heaven's gate. With Jim on trial to prove his selfless acts on earth, best friend Andy is summoned to heaven to defend him. As Jim attempts to prove his good works to God, his sister-in-law, Dana, represents the Devil, arguing that Jim's selfishness should mean a certain trip to hell.
It's Cheryl's birthday and Jim decides to buy her a diamond necklace. But in an attempt to save money, he buys the necklace from Andy's unreliable source and soon learns that it was taken off of a dead woman whose ghost now begins to haunt him.
Cheryl forces Jim to donate time to charity. His reluctance turns to elation when he's rewarded with a thousand-dollar check for his efforts. Cheryl insists he return the check, but Jim is itching to buy himself somthing frivolous with the money. And to really test Cheryl's integrity, he spends the money on a pricey designer handbag for her.
Jim uses his passion for sports to connect with son Kyle. But sports-challenged Kyle identifies more with fellow sci-fi nerd Andy, forcing a reluctant Jim to dress up as a Cyclops at a sci-fi convention in order to win his son back.
Jim's bad back has him on prescription pain pills which has him in an altered state and opens up an opportunity for the family to share information which usually would upset him.
Jim attempts to look cool in the eyes of Ruby and her friends, until he realizes that he may be undermining Cheryl's authority due to his behavior.
Andy ends up injured after playing snow football with Jim, so Jim helps Andy make it seem like he had a freak accident because Andy was previously warned by his girlfriend not to play the game.
Cheryl and her friends, eager to get an afternoon away from the kids, arrange a "Daddy and Me" group for Jim and other dads with young kids at their home. Jim makes the best of a potentially boring situation by turning babysitting into a sporting event--staging baby races where the dads bet on their kids and drink beer.
Andy, desperate to impress Mandy with the perfect birthday gift, turns to Jim for advice. Jim counsels against givivng fancy jewelry, urging Andy instead to give a sentimental gift to win her over. But Andy's recollection of what has meaning to Mandy is way off base, and instead of being pleased with the gift, she thinks he's cheating on her.
Jim prepares Kyle for his first "date" with Ruby's slightly older piano teacher, Mandy, whom Andy has fallen for and is secretly dating behind Kyle's back.
Jim becomes intrigued by Cheryl's raving about a yoga teacher so he decides to try out the class, only to end up impressed by the teacher. Both Jim and Cheryl end up taking separate private classes to relax from their busy family life.
Jim is convinced that an old flame wants to get back with him until he realizes that she wants to hook up with Andy, leaving Jim with a bruised ego.
Jim looks forward to a "guys only" weekend with Andy, but when Andy ends up dumped by Emily over a text message and when the guys stumble upon Emily's depressed ex husband, Jim decides to do his best to cheer up the guys and save what's left of their weekend.
When Cheryl learns of Jim's plan to use their twins in a movie starring Steve Guttenberg to get some money for Christmas gifts, she refuses to let him do it, but Andy and Jim decide to go through with the plan anyway, only to have it backfire when the producers cut the kids hair to make them look alike.
Jim urges Andy to propose to Emily or risk losing her, but when he sees Emily dining with another man, he doubts the wisdom of his advice.
Jim and his band win a chance to play for a child pop sensation Jami McFame, but when the star gives them an attitude, Jim decides to set her straight.
When Dana, Cheryl's sister and best friend, moves away, Jim realizes he must find Cheryl a new friend as soon as possible.
Jim guilts the older kids into doing household chores after Jonathan's special blanket goes missing.
