Doug, Carrie and Arthur head out to the airport to visit with Doug's parents while they have a short layover at Kennedy Airport on their way to Montreal. While there, his parents ask him to sign their living will, making him the one responsible for pulling the plug. When his sister Stephanie gets wind of this, she is offended that she wasn't the one asked to be responsible.

Doug's Uncle Stu asks him to get his son, Danny, a job at IPS. Doug doesn't want him working there but he doesn't want to look bad to the family so he instructs his boss to interview him but not hire him. Eventually, Doug feels guilty and goes back to O'Boyle to ask him to reconsider Danny for the job. Meanwhile, Arthur fills out audience comment cards on a new movie.

While cleaning out the Heffernan freezer, Carrie comes across the top tier of her and Doug's wedding cake, and reflects back to the time when they got married. As she takes a trip down memory lane, Carrie remembers her uneasiness prior to their wedding day and her desperation in needing a sign from God to be sure about the marriage. The priest calms Carrie's insecurity by informing her that she and Doug actually met years before when they were kids. Carrie feels that that's a "sign" from above, but Doug later learns that it was Danny, his cousin, whom she met, not him, and is afraid to tell her the truth. Also, Arthur convinces Doug's parents to cover the cost of the wedding, and then proceeds to spend all their money to make the day extra special.

Its Christmas time and Doug's parents are coming over. The only problem is that Doug and Carrie are trying to conceive because of Carrie's "fertile time." After trying to not tell his parents, Doug finally tells them of the situation and leaves the house for one night. That night, Doug can't perform because he is under pressure by his parents and Arthur.

Doug's parents visit while Carrie's on a business trip and take over running the house, making Doug feel like a kid again. Also, Arthur tries to strike it rich by inventing a new type of screwdriver called "the Arthur's head."

Doug and Carrie run into Doug's high school girlfriend, Margie, at his favorite sports bar. Carrie gets jealous when she discovers that Doug's mother would rather spend time with his ex-girlfriend than her. Margie and Doug fight over the song that Doug was meant to write for her back in high school. Doug, intent on redeeming himself attempts to write the song with help from Danny.

At a wedding, Doug takes a naughty picture with a disposable camera supplied by the bride and groom. After letting Danny take the blame, and after confessing to a priest, he has the dreaded task of coming forward with the truth.

A toy from their childhood leads to a rift between Deacon and Doug. Meanwhile, Carrie tries to give her father a great Christmas gift, but this proves hard to do when everyone thinks of the wrong gifts they are receiving, altering their original gift choices.

Carrie learns from Janet that Doug had a dog when he was 11, that they still have today, and Doug is 38! Janet admits to Carrie that the dog died, and they replaced it without Doug knowing.

During a romantic dinner, Doug is inspired to proclaim his love to Carrie. Carrie is taken by his gesture and suggests that they renew their vows. The two find that planning the wedding is much more troublesome than expected. The ceremony is on again, off again as Doug and Carrie are faced with endless complications, including finding a chimp to serve as Doug's best man. In the midst of the wedding planning Arthur is praying that his wedding present, aged Port wine, will go unused when he discovers the value of the fine wine on E-bay.

Carrie asks Deacon and Kelly to accompany her and Doug to Florida for their visit with the in-laws so that they'll be forced to stay at a hotel instead of with Doug's parents. What looks like a perfect vacation turns into a nightmare when spring breakers invade the hotel, forcing Carrie and Doug to reconsider their future accommodations when visiting the folks. Adding to the misery is the great disappointment shown by Doug's mom over the fact that no one is staying at her house.

Doug's parents pay a visit to the Heffernan household, where Doug surprises them with theater tickets. However, Joe Heffernan is distracted by his Train Fair, which causes Janet to develop a friendship with Arthur.

Doug and Carrie are roped into helping out at their church during the holidays: he guards the manger, while she tries to bake a cake. Also, Arthur and Spence attempt to write a Christmas song so they can cash in on the holiday.

After she beats him and his friends in a friendly poker game, Doug convinces his mother to try to enter a high-stakes tournament. Meanwhile, Carrie gets Spence to help her lose her accent to improve her chances of getting a promotion.