* Amara endures a number of depressing incidents in "[[http://www.platypuscomix.net/keiki/index.php?issue=5&pageType=index&seriesID=5 Freewheeling]]", especially when she discovers that [[spoiler: the time she became a popular trendsetter was AllJustADream]]. 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 [[http://www.platypuscomix.net/keiki/index.php?issue=14&page=21 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 [[MayflyDecemberRomance mortal]] Beefer.
* Arguably, the part of "Princess Pi vs. The Totally Nazis" when the Totally Nazis' [[http://www.platypuscomix.net/princesspi/index.php?issue=3&page=6 ceaseless insults]] appear to [[http://www.platypuscomix.net/princesspi/index.php?issue=3&page=7 push Pi]] over the DespairEventHorizon.
* "Princess Pi vs. CerebusSyndrome" plays most of Pi's overly grim stories [[PlayedForLaughs for laughs]], but the story of [[http://www.platypuscomix.net/princesspi/index.php?issue=11&page=8 the death of her mother]] feels genuinely sad.
* See TearJerker.TrueBelievers
* Peter's unending suffering in "[[http://www.platypuscomix.net/history/kellogg.html Kellogg Middle School: The Happiest Place on Earth]]".
* The "Concept Unification" video in "[[http://www.platypuscomix.net/kidzone/chucke.html 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 [[http://www.platypuscomix.net/darkvault/freespiritscript6.html declaration of success]] in finding a MissingEpisode of ''Series/FreeSpirit'' 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).