Scary Stories to Tell in the Dark not only has scary parts and endings, but also has sad moments to make said scary scenes even more disturbing.
- The ending of "The Bus Stop"
when Ed Cox finds out Joanna really died about 20 years earlier waiting in the rain by being hit by a car. - "The Hog". George S. Irving's narration amplifies the sadness, and the movie version even has sad violin music.
- As objectively karmic as Sandra and Delores' punishment at the end of "The Drum" is, it's hard not to feel sorry for the girls. Not only had they been deceived into doing horrible things for nothing, but their mother also abandoned them. The fact that they were pleading with both their mother and the gypsy beforehand doesn't help.
- "Harold" can be seen as this from a certain point of view. The titular, sentient scarecrow gets constantly abused by his creators (who, stupidly, dismiss his first grunt as an animal getting inside their scarecrow), grows into a vengeful monster, and eventually kills one of the farmers... by flaying him alive! It almost seems like a metaphor for the effects of child abuse.
- Just imagine "The Bride" from the groom's perspective. You're playing hide-and-seek, and your newlywed wife is nowhere to be seen, no matter where you look. Perhaps you think that she has abandoned the marriage... and then you find out, years later, that she was in that same church the whole time, and died on what was supposed to be one of the happiest days of her life.
- Imagining this from the bride's point of view is equally as sobering and crosses into Nightmare Fuel. The book even mentions that no one knows how long she was suffering for in the trunk, waiting for a rescue that never came.
- The ending of "The Bed By The Window". Richard killed George just so he could get the titular bed by placing George's heart medications away from him. And what does he see outside the window? Nothing but the brick wall of a next door building. It gets worse if you read the original story's ending: George is later revealed to have been blind and he pretended to see the things outside the window to cheer Richard up.
- "Cold as Clay" shares a similar plot to "The Hog" where it tells the romantically tragic story a farmhand named Jim falling in love with a farmer's daughter, then dying from a broken heart when she is sent away by her father. The farmer felt guilty for Jim's death, so he never told his daughter. Jim later rises from the dead as a Revenant Zombie, who takes the girl back to her father allegedly on his orders. She gives him a handkerchief when she feels his cold skin as they ride back to the farmer's house. When she tells her father that Jim sent her back, they dig up his grave, and discover his corpse still wearing the handkerchief.
