- Amara endures a number of depressing incidents in "Freewheeling", especially when she discovers that the time she became a popular trendsetter was All Just a Dream. Peter boasts in the Keiki archive that people called this the best comic he made up to that point, but doesn't explicitly say why.
- Darcy's rant about the media's romanticization of vampires in "Twilight Princess" includes a lament about the fact she can never have a romantic relationship with the mortal Beefer. "Love Stinks (Yeah Yeah)", released three years later, reveals that both Darcy and Beefer continue to hold romantic feelings for one another, but doubt that they can even see each other again.
- Arguably, the part of "Princess Pi vs. The Totally Nazis" when the Totally Nazis' ceaseless insults appear to push Pi over the Despair Event Horizon.
- "Princess Pi vs. Cerebus Syndrome" plays most of Pi's overly grim stories for laughs, but the story of the death of her mother feels genuinely sad.
TearJerker.Free Spirit 2014
- Peter's unending suffering in "Kellogg Middle School: The Happiest Place on Earth".
- The "Concept Unification" video in "The Chuck E. Cheese Story", detailing the transformation of a Showtime Pizza restaurant into a Chuck E. Cheese facility, includes a warning not to watch it because "it's too depressing".
- Peter's declaration of success in finding a Missing Episode of Free Spirit becomes bittersweet when he admits refusing to watch the episode right away, due to his realization that the sooner he finishes it, the sooner he'll completely run out of Winnie Goodwin exploits to enjoy (aside from his comics).