When Doug and Carrie are not invited to the block party, Doug shows up anyways and ends up adopting a dog to prove he is a good person. Doug finds out that a dog is a lot of work and tries to find a way to return it without looking bad, but before he can, Carrie tells him they have to keep the dog a little longer because their neighbor, Glenn, says he can get her a good deal on a massage chair.Arthur also tries to help Danny break his addiction to gambling, but ends up getting hooked on it too. (20:30)

When O'Boyle goes into rehab he asks Doug and Deacon to fill in for him as supervisor. Doug initially turns it down and tells Deacon to go for it, but then decides he wants it so that he can prove to Carrie that he is not content being a driver for the rest of his life. Soon Doug realizes he is in over his head when everything starts going wrong at the office. (20:30)

Deacon's son draws a picture of Arthur with crooked teeth, which leads Arthur to try to convince his family that he should get braces. Doug uses this idea to try to improve Carrie, by having Deacon's son draw a picture of her flat-chested. (20:30)

Everything is going smoothly between the newly formed friendships until Kelly grows tired of Doug's forgetfulness. With Kelly no longer available, Deacon and Carrie invite Doug to hang out with them, but Doug is so distraught over losing Kelly that he ruins their evening. Meanwhile, Arthur feels betrayed by the coffee shop girl, Gloria, who is having great success by taking Arthur's relationship advice and doing the exact opposite. (20:30)

Carrie convinces her female co-workers to blow off work and take advantage of the hotel's spa. However, her plans are put in jeopardy when Doug surprises her and wants to spend the weekend watching the original "Planet of the Apes" series. Carrie tries to convince Doug to go home since she's going to be working all weekend, but gets caught in the lie when he discovers she already has an appointment for a massage. Meanwhile, Danny and Spence sneak into the Huey Lewis concert by wearing Doug's "Event Staff" jacket, but their excitement quickly disappears when they are forced to fulfill several absurd requests for the band. (20:30)