Doug decides to buy a pumpkin to get into the Halloween spirit, but as soon as Arthur sees it, he smashes it and banishes the celebration of Halloween. Doug, frustrated by Arthur "forbidding" things, takes it upon himself to go all out with decorations and ends up scaring Arthur so badly that he nearly has a heart attack and ends up in the hospital. When Doug finds out about Arthur's traumatic childhood and the reasons why he hates Halloween, he feels guilty for what he has done and tries to make it up to him by driving around town, looking for Arthur's favorite childhood treat. Deacon, on the other hand, is determined to find his son Kirby a superhero costume, but is frustrated because there aren't any black superheroes. Deacon resigns himself to the fact that Kirby is gay because he turns down the Darth Vader costume so he can be a Power Puff Girl.

As Arthur prepares to undergo heart surgery, he asks Carrie and Doug to bring him his sleep mask. While digging through Arthur's closet for the mask, Carrie finds a box which contains an extensive scrapbook of her old finger-paintings, report cards, and school photos that Arthur has been keeping. As she is flipping through it, she finds an acceptance letter from Florida State University – which she has never seen before. Meanwhile, Doug makes friends with a quirky stranger in the hospital and soon regrets it.