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.

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.

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.

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.

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.