Episode: 026 | Aired: September 20, 1999
Doug gets a motorcycle, which causes a fight. Doug sells the motorcycle and tells Carrie he sold it because of her, but really he decided he hates it, and Carrie feels guilty.
Episode: 027 | Aired: September 27, 1999
Carrie doesn't have many friends, so Doug finds her one, but then Carrie starts spending too much time with her.
Episode: 028 | Aired: October 04, 1999
Doug is goofing off at work, and ends up with a staple in his "area". He has to suffer through the pain while at a meeting with a banker because of an argument with Carrie.
Doug calls Arthur a demented old circus monkey and Arthur overhears it. Later Carrie is doing an impression of him and he walks in on that. To make up for it Doug decides to bring Arthur to a Mets game he won tickets for after being named employee of the month. While trying to make Arthur happy both Carrie and Doug wind up in jail.
Episode: 032 | Aired: October 18, 1999
Carrie leaves the garage door open and Doug's TV gets stolen.
Episode: 033 | Aired: November 01, 1999
Doug, Carrie, Deacon, and Kelly go on a vacation together. While at the hotel, Doug and Carrie find out that Deacon and Kelly have a more active sex life than them.
Episode: 034 | Aired: November 22, 1999
Carrie's friend and her husband are over for dinner and Carrie invites them to spend Thanksgiving weekend with them. Doug hates her husband, so he convinces Spence to move out and stay with them so Carrie's friends can't.
Episode: 035 | Aired: November 15, 1999
A waitress at Cooper's asks about Doug's situation, and Doug decides he should start dressing better.
Episode: 036 | Aired: November 29, 1999
Doug's bowling team sponsor is threatening to stop paying if they don't start winning. The only bad player on the team is Carrie, so Doug has to decide if he will replace her to win.
Episode: 037 | Aired: December 13, 1999
Doug gets a $3,000 dollar Christmas bonus and Carrie wants to invest it in the stock market. Doug can't handle it and keeps getting nervous when it falls.
Episode: 038 | Aired: January 17, 2000
Doug invites his old football teammates over so they can talk to a reporter about their team. Doug made a championship winning play, but people on the team think another player made it, so Doug tries to prove them wrong.
Episode: 039 | Aired: January 24, 2000
Cold weather comes and Arthur has to move upstairs. When the weather warms up he stays upstairs, and Doug and Carrie want him back in the basement.
Episode: 040 | Aired: January 10, 2000
Carrie tries to convince Doug to be the best man at Danny's wedding.
Episode: 041 | Aired: February 07, 2000
Doug catches Carrie cheating at board games, so he tries to find what is making her cheat.
Episode: 042 | Aired: February 21, 2000
Doug and Carrie meet a new couple to be friends with. When their schedules get messed up, they invite Deacon and Kelly over at the same time. Then they start to worry that Deacon and Kelly are stealing their friends.
Episode: 043 | Aired: February 14, 2000
Doug and Carrie think back to the first time they met. Doug was working as a bouncer at a club and Richie convinced Carrie and her friend to go out with them. Carrie was Richie's date, but she hated him, and Doug's date liked Richie.
Episode: 044 | Aired: March 06, 2000
Deacon and Doug go to Atlantic City and Doug loses a lot of money, while Deacon makes a lot. Deacon used money that he was holding for Doug to win the money, so Doug wants some of it.
Episode: 045 | Aired: February 28, 2000
Doug has to take Arthur out of the house so Carrie can set up for his surprise party for his 75th birthday. While at a restaurant, Doug loses Arthur.
Episode: 046 | Aired: April 17, 2000
When Doug finds out that Deacon is a big brother for a kid, Doug signs up to be one too. But when he gets the kid, he decides he doesn't like him.
Episode: 047 | Aired: May 01, 2000
Tim Sacksky convinces Doug to join his water filter selling business. It turns out to be nothing more than a pyramid scheme and Carrie wants Doug to go get his money back, but Doug still thinks he can make money.
Episode: 048 | Aired: May 08, 2000
Doug takes Carrie to an Italian restaurant he found, but Carrie thinks the waiter was rude to her and forbids Doug to go again. Doug loves the restaurant, so he decides to sneak behind her back.
Episode: 049 | Aired: May 22, 2000
Doug and Carrie can't decide what to do about their vacation.
Episode: 050 | Aired: May 15, 2000
Doug shows Carrie he can still be romantic, and Arthur get jury duty.