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Deacon and Kelly don't want Doug around Major anymore after he inadvertently scares him, and Arthur begins a new business selling senior citizen services to carpoolers.
Carrie gets upset because one of her fellow secretaries "steals her moxie" and gets a promotion, and everything at IPS falls apart after Doug temporarily takes over the office.
Things get out of hand as Doug frantically tries to stop a woman who claims to have spent a romantic weekend with him from calling the house.
When Carrie insists that Doug figure out how to invest their tax return check, Doug decides to buy an ice cream truck from a stranger.
Carrie is finally fed up with Arthur, so she decides to put him in a retirement home. Doug, of course, is excited but after a touching story told by Arthur, Doug tries to decide whether or not Arthur should go.
Doug befriends a driver from one of IPS' competitors, but eventually discovers it's just a ruse to make him the butt of a joke.
Doug crashes Carrie's weekend company retreat, not realising she's blown it off for a relaxing day with her girlfriends.
Doug and Deacon discover they have more in common with each other's wives than their own, so they start hanging out with each other's wives as well.
It's Doug's 40th birthday and Carrie begins to try to make Doug realize that he should start wanting to do more with his life. So Doug decides he wants to ride a roller coaster that he was to afraid to ride when he was younger.
While they're having dinner at a restaurant a man who's in wigs tells Doug Carrie's hair is worth $3,000 dollars.
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