Doug's cousin Danny is getting married but Danny does not have a best man. Carrie volunteers Doug as the best man. So now Doug is on the hook and worries about giving the speech and has to set up a bachelor party. Sadly Danny doesn't have too many friends so the party has many empty seats, and to top it off the stripper isn't 100% either!
Doug invites his old high school championship football team to his house to have a party. Doug tells Carrie that he got a huge block to set up the winning touchdown. While talking to a reporter about how they won the game, the team remembers Doug's teammate Tom Busterman, who is confined to a wheelchair, making the block. Doug gets the game tapes from the attic, and has the team watch the play. Doug was given Busterman's jersey by mistake that game, and that's why they got the players mixed up. Doug was the real hero.
Because it's very cold, Arthur gets to sleep in Carrie's office, which is right across Doug and Carrie's bedroom. Doug doesn't like this and can't wait for some warmth so Arthur can get back to his basement.
Arthur's 75th birthday is coming up and Doug and Carrie decide to throw him a surprise party, but their in for a rude awakening when two of the invited guests are at each others throats and they can't find Arthur!
Doug and Carrie go to a new Italian restaurant where Carrie gets a wrong order and causes chaos there. Doug gets very upset because he loved the food and he wanted that place to be his and Carrie's new restaurant. Carrie bans Doug from there, so Doug has to start sneaking behind her back to eat there.
Doug sees someone driving an R.V. and decides he wants to buy one for himself and Carrie's vacation, however Carrie is planning a trip to Paris for their vacation. So in deciding where to go, they flip a coin.
When Doug learns that Carrie is buying him clothing from the "Big and Tall Shop", he is now determined to lose weight. While he is on his journey to lose weight, he tells Carrie that she needs to make some changes to her lifestyle as well. Meanwhile, Arthur is trying to keep the family safe by getting a safety dummy.
When Carrie spends a night out with some of her colleagues, she finds out that they are more successful then she is. Carrie never went to college. Now, she is trying very hard to get back to school and get a good education to become more successful. But will she be able to balance work, school, and family at the same time?
While Doug's company is in strict negotiations, he decides to buy a brand new SUV. When Carrie finds out, she demands him to take it back. At this time, IPS has gone on strike. Now Doug is out of work.
It is week two of the IPS strike, and Doug still has not gotten a job. To get back on his feet, his sister Stephanie get him a substitute teacher job at her school. However, it is a high school, and the kids are not so nice. Can Doug survive?
It is week three of the IPS strike, and Doug has just been hanging around the house for all three of them. Deacon has also been out of work and Kelly has had enough of his laziness. Carrie and Kelly decide to have Arthur, Doug, and Deacon spend the whole day together. However, their plan backfires, because the three of them become uncontrollable delinquents. In the end, the strike is ended.
When Kelly's great aunt dies, both Deacon and her have to go to Chicago and they have no one to watch their two kids, so Doug and Carrie offer to watch them while their gone. When they first start watching the kids Carrie was terrified of the idea, but soon after they began to love the idea, up until Kirby catches Doug and Carrie being intimate in their parent's bed.
It's the Christmas season and the Heffernan's see that they have a new neighbor who happens to be Lou Ferrigno. Arthur wants Lou to read his screenplay to get it produced. Doug decides to buy Carrie a camera the only problem is that her boss at work also bought her a camera which happens to be nicer.