In an attempt to go to Las Vegas for a weekend with the guys, Doug begins to build up credit by taking Carrie to a spa. Meanwhile, after hearing about Las Vegas, Arthur trains Spence on how to count cards, before visiting a small casino, being held for orphans.
On the way to a overeating support group, Doug notices an abusive relationship group, and decides to join them instead. Although, Carrie becomes suspicious when he not only gains weight, but begins to cower in her presence.
Doug's position as the "Funny Guy" is threatened, when IPS' new employee wins over the workforce with his impersonations. Meanwhile, an assistant is hired to work for Carrie, and ends up performing more work than expected.
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.
While Christmas shopping at the mall, Doug loses his wallet and begins a quest to find the wallet and the culprit who may have stolen it. But with no help from Carrie or the cops, he requests the help of Arthur.
After ten years of marriage, Doug finds a new love – in the form of designer cologne that Carrie can't stand, but his scent-ual affair forces Carrie to demonstrate bad behaviors of her own. Meanwhile, Arthur attempts to show Spence and Holly the finer points of movie hopping.
Carrie uses her extra income to hire a maid, but Doug feels left out and decides to hire his own help in the form of Spence's mom, Veronica. Soon, Veronica proves to make more messes than she cleans, especially when her newly subordinate position makes Arthur pine for her.
Doug decides to pursue a long-abandoned dream to become a bartender, much to Carrie's angst. Although she starts to warm up the the idea, Doug soon realizes that dreams are not always what they are cracked up to be. Meanwhile Arthur enters the dangerous world of politics.
Carrie recalls what Doug said to her when they were dating that made her want to marry him, but then she learns a horrifying truth about that night; Danny falls for Holly after his girlfriend breaks up with him
When delivering a package to his old high school, Doug meets his old football coach, and against Carrie's wishes, begins to return to the school on a regular basis as the football hero.
Meanwhile, after losing his eye drops, Arthur manages to lose his sense of hearing, sight, and speech in one day and becomes completely reliant on Holly.
Carrie is discouraged about her looks as she faces her 35th birthday so Doug gets construction workers to hoot and holler at her as she passes by in hopes of cheering her up. Also, Arthur tries to come up with a perfect gift for his daughter.
When Deacon snubs his usual boys for a new African-American friend, Doug desperately tries to find his own "roots" in an attempt to win him back. Meanwhile, Carrie runs her cuticles ragged to find out why her manicurist will no longer schedule her appointments.
What starts out as a great trip quickly turns into a nightmare as Doug and Arthur are forced to switch planes, which puts them in Pittsburgh instead of St. Louis.
While eating at a new cafe with Deacon, Doug manages to agitate their waitress so much that she demands they fight once her shift ends. Meanwhile, Carrie asks Holly to go shopping with her, only so that she can use her van.
When a checkout girl is distracted making personal calls and accidentally doesn't charge Carrie for her digital music player, Carrie walks out the store with free merchandise.
A work event in a ballpark skybox leads Carrie, Doug and his buddies out to the game - but when an important client finds fault with Doug, Spence has to step in as the devoted husband. At Arthur's dinner party, guest Bernard, turns the table against him.
Doug lures Carrie to a timeshare sales ski weekend where the strength of their relationship is tested under the intense sales pressure. On the same excursion, Spence and Danny feel the sting of intolerance when they assume the role of a "couple" to enjoy the weekend.
Doug reluctantly agrees to Carrie's idea to "flip" their deceased neighbor's house but doesn't hesitate to blame her when the cost of the much-needed home improvements start to add up.
