September 21, 1998 8:00 pm
Doug receives his new big screen TV and turns the basement into a private recreation room. However, after the death of the wife of Carrie's father and the subsequent burning down of his house, Arthur and Carrie's sister Sara move in. So Doug's recreation room becomes Arthur's new room, and the big TV moves to the bedroom.
September 28, 1998 8:00 pm
Stunned by an old photograph of Carrie's mother, Doug convinces Carrie to go on a diet and must pretend he is going on one too.
October 5, 1998 8:00 pm
Carrie's on the fast track at her new job in a Manhattan law firm. But the trappings of success – late nights at the office, free concert tickets and being surrounded by bright, dynamic people – make Doug wonder why she ever ended up with a guy like him. While painfully succumbing to boredom at a cello concert, he discovers that, despite his lowbrow tendencies, Carrie never has and never will feel she "settled" by marrying him.
October 12, 1998 8:00 pm
Doug can't figure out why Carrie refuses to go on a double date with Richie and his wife, Marie.
October 19, 1998 8:00 pm
Doug and Carrie throw a wedding anniversary party for themselves. Doug invites his aunt, and finds out that his aunt and uncle are having problems. When Arthur meets Doug's aunt, he falls for her. Carrie eventually lets him date her, but ends up regretting it, leaving Arthur with plans to propose to her.
October 26, 1998 8:00 pm
After feeling bad that Arthur has no friends, Doug starts taking Arthur everywhere with him.
November 2, 1998 8:00 pm
Doug and Carrie remember when he proposed to her after a jeweler offers more money for the ring than Doug had originally paid.
November 9, 1998 8:00 pm
Carrie signs her and Doug up for a class at the community college when she begins to think that they're becoming dumb and boring. Doug has a hard time with it, but luckily Spence in also in the class...
November 16, 1998 8:00 pm
Doug regrets helping Ray Barone cheat on his driving test. Meanwhile, Arthur's neediness hinder's Carrie's studying.
November 23, 1998 8:00 pm
Carrie has Thanksgiving Day planned but is guilted into making a homemade meal which leaves her with less than a day to make a meal for ten people.
December 14, 1998 8:00 pm
Doug and Carrie realize they must buy a new car after theirs breaks down. One problem: they can't afford it.
December 21, 1998 8:00 pm
Carrie fixes Spence up on a blind date with one of her co-workers.
January 11, 1999 8:00 pm
Doug and Carrie attend a wedding of an old flame of Carrie's, creating an uncomfortable situation for Doug.
January 18, 1999 8:00 pm
The Heffernans' new neighbors have a dog that keeps them up at night, but Doug wants to avoid confrontation. Arthur thinks Charles Schultz is using him as a template for Peanuts characters.
February 1, 1999 8:00 pm
Carrie is upset about getting older when her 30th birthday rolls around.
February 8, 1999 8:00 pm
Doug's romantic plans with Carrie are hijacked by Veronica, who has planned a last-minute surprise party for Spence. Arthur meets a woman at a Senior Center dance.
February 15, 1999 8:00 pm
Carrie gets a speeding ticket and Doug, out of fear of the car insurance doubling, convinces her to go on a date with the cop that gave her the ticket.
February 22, 1999 8:00 pm
Doug begins to miss being behind the wheel of his truck when he is promoted after the death of his shift supervisor.
March 1, 1999 8:00 pm
When Ray Barone calls and asks Doug if he wants to play golf at his private club, Doug cancels on his friend Richie – who he was going to spend the day with in order to comfort him after his divorce. But when a huge thunderstorm lets loose, Doug's day of golf turns into a fiasco, and he high-tails it back to his garage to Richie. Meanwhile, Ray's mother, Marie, arrives at the Heffernan's early to pick Ray up and gives Carrie a lesson in cleaning – which Carrie milks for all it's worth.
March 15, 1999 8:00 pm
Doug is upset when his new trainee doesn't make Carrie jealous; Meanwhile, Arthur must deal with his purchase of his tombstone in advance and changing the first two numbers of his death year from 19 to 20.
April 5, 1999 8:00 pm
Carrie's boss is having a cocktail party to impress a client and the only way Doug made it there was by not eating anything all day. He embarrasses Carrie by searching for food after he finds out there's no food at the party; Meanwhile, Arthur and Spence have trouble while planning a new business.
April 26, 1999 8:00 pm
Carrie isn't happy that Doug's invited the Sackskys over-until she learns they're separating and offering them their Hamptons time-share. Meanwhile, Arthur seeks answers from an ointment company after developing a nasty rash.
May 3, 1999 8:00 pm
Doug and Carrie send Arthur off to work at cousin Danny's pizza restaurant.
May 10, 1999 8:00 pm
Arthur almost gets Doug fired. Doug then releases all his feelings about Arthur, which results in him moving out of the house.
May 17, 1999 8:00 pm
Doug and Carrie consider having a baby, which results in a flashback from Arthur about the day that Carrie was born.