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| Episode 1 - [Queasy Rider] |
| Details : Against Carrie's wishes Doug buys a motorcycle which causes them to have a huge fight; Meanwhile Arthur gets a job at a pretzel store. |
| Guest Cast and Crew : Don Harvey as Dirk | |
| Air Date : Sep. 20, 1999 | Rating ➦ ★★★★★★ |
| Episode 2 - [Female Problems] |
| Details : Doug feels left out after Carrie becomes friends with a new neighbor. |
| Guest Cast and Crew : Myndy Crist as Jessica | |
| Air Date : Sep. 27, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 3 - [Assaulted Nuts] |
| Details : Doug while goofing off at work accidentally ends up with a staple wound to the scrotum. |
| Guest Cast and Crew : Nelson Mashita as Dr. Churnin | Mason Canter as Pete | Lillian Hurst as Maria | Jeanine Jackson as Rhonda Phillips | Brian Paul Stuart as Orderly | |
| Air Date : Oct. 04, 1999 | Rating ➦ ★★★★★★★★★ |
| Episode 4 - [Parent Trapped] |
| Details : Deacon And Kelly ask Doug And Carrie to be the godparents of their baby; Arthur runs into trouble at the pretzel store when he is put in charge. |
| Guest Cast and Crew : Manu Intiraymi as Zack | Philip Bolden as Kirby Palmer | Frantz Turner as Bill Gilliard | Joe Marinelli as Neal | Jeremy Guskin as Kenny | Nancy Yee as Rita | Seth Menachem as Tony | |
| Air Date : Oct. 11, 1999 | Rating ➦ ★★★★★★★ |
| Episode 5 - [Tube Steaks] |
| Details : Carrie leaves the garage door open and Doug's big screen TV is stolen. |
| Guest Cast and Crew : Marv Albert as Himself | |
| Air Date : Oct. 18, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 6 - [Doug Out] |
| Details : Arthur's inclusion at an outing to a Mets game creates problems for Doug. |
| Guest Cast and Crew : Rock Reuben as Drunk Guy | Sandy Marks as Refreshment Guy | Richie Minervini as Security Guard #1 | Barbara Savage as Waitress | James Wong as Security #2 | |
| Air Date : Oct. 25, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 7 - [Get Away] |
| Details : Doug and Carrie along with Deacon and Kelly go on a weekend trip. While there they find out that Deacon and Kelly have a very active sex life. |
| Guest Cast and Crew : Bill Wiley as Burt | Writer : Tony Sheehan | |
| Air Date : Nov. 01, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 8 - [Dire Strayts] |
| Details : Doug and Carrie invite Ray and Debra Barone over for dinner. |
| Guest Cast and Crew : Patricia Heaton as Debra Barone | Ray Romano as Ray Barone | Robert Brooks as Chenz | Jason Packham as Eric | |
| Air Date : Nov. 08, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 9 - [I Candy] |
| Details : A waitress flirts with Doug which causes him to start acting strange. |
| Guest Cast and Crew : Idalis DeLeón as Jill | |
| Air Date : Nov. 15, 1999 | Rating ➦ ★★★★★★★ |
| Episode 10 - [Roamin' Holiday] |
| Details : In an attempt to get away from Carrie's friends for Thanksgiving Doug invites Spence over. |
| Guest Cast and Crew : Ben Bode as Mike | Melissa Samuels as Susie | |
| Air Date : Nov. 22, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 11 - [Sparing Carrie] |
| Details : Due to financial trouble Doug's bowling team must win the next game. Doug must help Carrie to improve her bowling ability or kick her off the team. |
| Guest Cast and Crew : Robert Klein as Bruce Degner | Kymberly Kalil as Annette | Ellen Ratner as Pam | |
| Air Date : Nov. 29, 1999 | Rating ➦ ★★★★★★★ |
| Episode 12 - [Net Prophets] |
| Details : Carrie wants to invest Doug's Christmas bonus; Arthur competes with the neighbors about who has the largest yard decoration. |
| Air Date : Dec. 13, 1999 | Rating ➦ ★★★★★★★★ |
| Episode 13 - [Party Favor] |
| Details : Carrie convinces Doug to be the best man at his cousin's wedding. |
| Guest Cast and Crew : Bas Rutten as Emil | Gary Valentine as Danny Heffernan | Jon Manfrellotti as Gianni | Marta DuBois as Eva | Marie Delprete as Camaro Epstein | Mookie Barker as Klaus | Mia Drake as Waitress | Billy Beck as Joe | Writer : Kevin James | |
| Air Date : Jan. 10, 2000 | Rating ➦ ★★★★★★★ |
| Episode 14 - [Block Buster] |
| Details : Doug has his old football teammates over; Meanwhile Spence tries to get his revenge on the football players for what they did to him in high school. |
| Guest Cast and Crew : Billy Gardell as Billy Kelner | Pat Finn as Tom Busterman | Mookie Barker as Coach Prudente | Mauricio Mendoza as Michael Cedeno | Andy Mackenzie as Bill Dwyer | Jason Beck as Derrick Broadnax | Writer : Tony Sheehan | |
| Air Date : Jan. 17, 2000 | Rating ➦ ★★★★★★★ |
| Episode 15 - [Frozen Pop] |
| Details : Arthur is moved upstairs to Carrie's office once the weather gets cold but have problems when the weather warms up and Arthur thinks his move was permanent. |
| Air Date : Jan. 24, 2000 | Rating ➦ ★★★★★★★ |
| Episode 16 - [Fair Game] |
| Details : When Carrie is caught cheating at a board game twice they trace her cheating problem back to when she was a child. |
| Guest Cast and Crew : Sandra Taylor as Donna | Madison Lanc as Young Carrie | |
| Air Date : Feb. 07, 2000 | Rating ➦ ★★★★★★★ |
| Episode 17 - [Meet By-Product] |
| Details : Doug and Carrie recall the first time they met. |
| Guest Cast and Crew : Kara Zediker as Lynn | Donny Osmond as Himself | Laura Otis as Nicky | Jason Packham as Patron | |
| Air Date : Feb. 14, 2000 | Rating ➦ ★★★★★★★ |
| Episode 18 - [The Shmenkmans] |
| Details : Doug and Carrie make new friends and by a scheduling mix-up the new friends and Deacon and Kelly end are invited to the same dinner party. And in the end they have no friends. |
| Guest Cast and Crew : Sean O'Bryan as Marc | Philip Bolden as Kirby Palmer | Bob Kirsh as Gary | Tina Morasco as Kim | Elisa Taylor as Abby | Michael Caldwell as Waiter | Marc Goldsmith as Russ | |
| Air Date : Feb. 21, 2000 | Rating ➦ ★★★★★★★ |
| Episode 19 - [Surprise Artie] |
| Details : Doug must keep up with Arthur while Carrie organizes his 75th birthday surprise party. When Doug loses Arthur Carrie must find him. |
| Guest Cast and Crew : Orson Bean as Carl Tepper | Harold Gould as Irv | Edith Fields as Mrs. Hanley | Jason Peck as Waiter | |
| Air Date : Feb. 28, 2000 | Rating ➦ ★★★★★★ |
| Episode 20 - [Wild Cards] |
| Details : Doug loses a lot of money when he and Deacon go to Atlantic City to gamble. |
| Guest Cast and Crew : Gregory White as Mr. Berenson | Dom Magwili as Manny | Mary-Margaret Lewis as Mary | Ralph Ahn as Foreign Man | Writer : Tony Sheehan | |
| Air Date : Mar. 06, 2000 | Rating ➦ ★★★★★★★ |
| Episode 21 - [Big Dougie] |
| Details : Doug becomes a Big Brother. Which leads him to running a 10K race to support heart disease; Carrie accidentally tells another Doug she loves him. |
| Guest Cast and Crew : Brady Corbet as Stu | Andrew McFarlane as Eddie | Hugh Holub as George | Alex Skuby as Lawyer Doug | Brendon Ryan Barrett as Jason | Cyndy Lu as Barbara | Daryl Keith Roach as Announcer | Writer : Michael J. Weithorn | |
| Air Date : Apr. 17, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 22 - [Soft Touch] |
| Details : Doug gets pulled into a water filter scheme thanks to his neighbors. |
| Guest Cast and Crew : Bryan Cranston as Tim | Ford Rainey as Mickey | Dee Dee Rescher as Dorothy | Gary Valentine as Danny Heffernan | Writer : Tony Sheehan | |
| Air Date : May. 01, 2000 | Rating ➦ ★★★★★★★★★ |
| Episode 23 - [Restaurant Row] |
| Details : Carrie forbids Doug to eat at his favorite Italian restaurant. |
| Guest Cast and Crew : Cosimo Canale as Carlo | Nino Del Prete as Antonio | |
| Air Date : May. 08, 2000 | Rating ➦ ★★★★★★★ |
| Episode 24 - [Flower Power] |
| Details : Doug shows his romantic side as Carrie thinks he has lost it; Arthur serves on a jury. |
| Guest Cast and Crew : Melissa Chan as Kim | Christine Gonzales as Amy | Michael Blieden as John | Cynthia Szigeti as Florist | |
| Air Date : May. 15, 2000 | Rating ➦ ★★★★★★★★ |
| Episode 25 - [Whine Country] |
| Details : Doug and Carrie face problems when they try to decide where to go on vacation. |
| Guest Cast and Crew : Eric Keenleyside as Roger | Dan Desmond as R.V. Bob | Tyler Hendrickson as Young Doug | |
| Air Date : May. 22, 2000 | Rating ➦ ★★★★★★★ |