Though the fanfic series provides entertainment, it also sometimes provides moments of sadness.
- Anytime there is a tribute to someone who has passed on.
- In "The Italian Gene", Romeo performs a Heroic Sacrifice in order for the heroes to escape.
- When Twilight Sparkle in "Disowned" tries to cope with Spike's temporary leave to Pinkie Pie. Granted, it lasted only for an episode, but Twilight's reaction to losing Spike is pretty hard.
- In Less Percent, Swiper loses most of his toys because of what Lotso, the actual real deal in Toy Story 3 had done to each of them and almost killed some of his friends in the process. After the ordeal is over and Lotso is finally destroyed for good, Brer Fox, of all people only has these words.
- Brer Fox: I ain't yur granpappy, Swiper...But I wish I is...
- Which also doubles as Heartwarming in Hindsight.
- The adaption arc of The Nutcracker Prince takes the cake as it shows how bad the fight between someone you desired for revenge and the person you believed to have betrayed their friendship is.
- Scary as it is, what also becomes sad to watch is Swiper and the Mouse King, Hiram, both whom had a very close friendship together, fighting against one another during the fight.
- In The SSSSS Squad's Big Score, Pinkie Pie becomes hurt when not only is she outright rejected by a pony named Pinkademia, but also her friends hang with her more, causing her to be depressed.
- It gets worse as when the reveal shows that all this time, Pinkademia was actually a paradox copy of Pinkie whom got herself killed saving her friends. Pinkie herself takes her death the hardest.
- Br'er Fox's life with his adopted uncle, Pinky, is a walking tearjerker, especially considering the abuse he takes from him.
- Rasticore's guilt of his obsession for an energy drink causes Ryoko, Strong Bad, and Hotaru to have kidney failure, believing it was his own fault and his confession on not only about losing his comrades, but especially Hotaru (who he views like a daughter) like he lost Toffee.
