Episode: 002 | Aired: October 26, 1998
After feeling bad that Arthur has no friends and nothing to do, Doug takes him out with him and his friends. Carrie is very "appreciative" and Doug tries doing it more to see how "appreciative" she will be.
Episode: 003 | Aired: September 28, 1998
Doug sees an old picture of Carrie's mother. She was young, hot, and skinny, just like Carrie. But then he sees another with her bigger than him. Afraid this might happen to Carrie he tries to trick her into dieting with him.
Episode: 004 | Aired: October 12, 1998
Carrie refuses to go on a double date with Richie and his new girlfriend and Doug wants to know why.
Episode: 005 | Aired: October 05, 1998
Doug begins to wonder why Carrie would ever settle for a pathetic guy like him when Carrie starts doing well at work.
Episode: 006 | Aired: October 19, 1998
Arthur wants to go out with Doug's aunt Sheila, and Doug is bothered by this, because he wants Sheila to go back to his uncle.
Episode: 007 | Aired: November 02, 1998
A jeweler offers way more money for Carrie's ring than Doug originally paid, and they debate whether to sell it.
Episode: 008 | Aired: November 16, 1998
Doug gets caught helping Ray Barone with a driving test and loses his license for a week. Ray tries to make it up to Doug and Doug ends up losing it longer when he is caught driving Ray's car by Ray's brother Robert, a cop.
Episode: 009 | Aired: November 09, 1998
Doug and Carrie are talking to a salesman when he uses a word they do not know. Carrie is bothered by this and decides it is time for them to try to become smarter, and they sign up for a reading class together which ends up being more than Doug can handle.
Episode: 010 | Aired: November 23, 1998
Carrie plans on making a simple thanksgiving dinner, but Arthur guilts her into making a big dinner like her mother used to.
Episode: 011 | Aired: December 21, 1998
Carrie fixes Spence up with a friend from work. Like TV Land on Facebook!
Episode: 012 | Aired: February 01, 1999
Carrie's thirtieth birthday comes and she doesn't like getting older.
Episode: 013 | Aired: December 14, 1998
Doug's car breaks down and he has to buy a new one, but he can't afford it.
Episode: 014 | Aired: January 11, 1999
Doug and Carrie go to a wedding of an old male friend of Carrie's. But Doug finds that she had sex with him and when Deacon says that he would be upset about it too to his wife, he finds out he had her too.
Episode: 015 | Aired: January 18, 1999
The neighbors have a dog that won't stop barking; Carrie says she'll go take care of it. Doug goes instead, after convincing Carrie he can be mean too, but he finds out he is walking their dog at night to keep him from barking.
Episode: 016 | Aired: April 05, 1999
Doug goes to a cocktail party Carrie's boss is having, but to get there he has to skip eating that day. When Doug gets to the party, he finds out there is no food.
Episode: 017 | Aired: February 15, 1999
Carrie gets a speeding ticket and Doug wants Carrie to go out with the cop to make the ticket disappear.
Episode: 018 | Aired: February 08, 1999
Doug plans the perfect Valentine's day, but first he has to take Spence out for a beer with his friends, because his birthday is on Valentines day. Spence's mom is secretly planning a surprise party, and ropes Doug, Deacon, and Richie into staying. When Spence gets there he storms off because his mom embarrasses him, and the guys have to stay because Spence's mom guilts them into it.
Episode: 019 | Aired: February 22, 1999
Doug's supervisor is in the hospital and Doug is temporarily promoted to his position. Doug ends up hating working behind a desk and misses his truck. But the supervisor dies and Doug is stuck.
Episode: 020 | Aired: March 01, 1999
Ray Barone calls and asks Doug if he wants to go golfing at his private club, but Doug already has plans with Richie. Doug cancels and tells Richie to come back later and they will watch TV, but when a storm comes and Doug and Ray are stuck in the clubhouse, Doug wonders if he can make it in time.
Episode: 021 | Aired: March 15, 1999
Doug has a hot woman as a trainee and he is upset that this is not making Carrie jealous. Arthur has to find a way to change the date of death on his pre-purchased tombstone so the first numbers are 20 and not 19.
Episode: 022 | Aired: May 03, 1999
Arthur is always getting in the way of Doug and Carrie's fun so they decide to try to pawn him off on somebody for a weekend. After they can't get anyone else to do it, Doug calls his cousin Danny who he hates and gets Arthur to work at his pizza place and stay with Danny for a weekend, but then Danny wants to hang out with Doug more.
Episode: 023 | Aired: April 26, 1999
Doug and Carrie have always hated their neighbors, the Sackskys. When the Sackskys offer Doug and Carrie their time share in the Hamptons because they are having marital problems, Doug and Carrie decide they have to be nice until they get the keys.
Episode: 024 | Aired: May 17, 1999
Doug and Carrie are thinking of having a baby.
Episode: 025 | Aired: May 10, 1999
Arthur almost gets Doug fired, so Doug yells at him, and Arthur moves out of the house. Arthur ends up living in a great apartment that he could never afford, and Carrie has to convince him to move back.