- Every negative thing Ramona goes through in Ramona the Pest, since it's shown from her perspective.
- When she goes outside to play a game called Gray Duck, she pulls Susan's hair and means it as a joke, but it hurts her. This prompts Miss Binney to assume Ramona was malicious put her on the bench to sit and do nothing while the other kids have fun. And after a whole game's worth of inactivity, she has to take a nap. Having outgrown naps, Ramona pretends to snore, which wakes up the others, who also pretend to snore. This leads to her being called "the worst rester" and being the last person allowed to get up. On top of all that, when she is still sulking from that incident (which was, it bears repeating, frustrating due to the sheer amount of forced inactivity and misjudgment), the adults assume she's worn out.
- Ramona getting suspended and being called a "kindergarten dropout".
- Howie has a bit of bad luck in this book too: he doesn't have dirt or trikes to play with (and Ramona doesn't sympathize and tells him they're for nursery), then he has to wear a Halloween costume he dislikes.
- The death of Picky-Picky, the family cat in Ramona Forever.
- Same book, Ramona and Beezus's tiff. Ramona wants to ride Howie's bike, but Beezus says no. Ramona yells at her and runs off to ride the bike anyway, calling Beezus "Pizzaface". The real reason Ramona chose this insult was because they had recently eaten pizza, which they don't normally get to eat, and her usual insult is "Pieface", which is not really meant to be offensive. However, Beezus, who is going through an insecure phase, thinks Ramona meant her face was red and blotchy like pizza sauce. Instead of asking for clarification, she just cries, and Ramona feels guilty because she was just going for a variation on Pieface. Ramona does fall off Howie's bike and tells Beezus, but she's sulking because of the Pizzaface misunderstanding, but Ramona thinks that she is glad that she's injured. And when they make up, it's during their cat's funeral.
- Ramona's Heroic BSoD after thinking her teacher thinks she's a nuisance in Ramona Quimby, Age 8.
- In the same book, Ramona feels unwell and throws up in class. It turns out to be stomach flu. For readers who are huge suckers for the Sick Episode trope, this can be very tearjerking, especially when Ramona thinks back to her teachers nuisance comment and feels like she really is a nuisance for throwing up.
- In "Ramona and Her Father," Ramona needs a sheep costume for the church Christmas pageant. Her mother, already stressed, mentions this to Dad when the girls are supposed to be in bed. Dad then says, "We don't want a spoiled brat on our hands," causing Ramona to conclude her father thinks she is one.
- During "Ramona the Brave," the class' Halloween project is making owls from paper bags. Ramona, who seems to have inherited her dad's gift for art, makes a great one. However, Susan copies it. Worse, Mrs. Griggs assumes Susan made the original and praises her in front of the class. Ramona retaliates, scrunching up Susan's owl. Mrs. Griggs' response is to make Ramona apologize to Susan in front of the entire class.
- In Beezus and Ramona, Beezus, who is nine at the time, experiences real angst over the fact she sometimes does not love Ramona. She assumes this makes her a horrible sister, but fortunately Aunt Bea is there to clear that up.
Tear Jerker / Ramona Quimby