- Bogan's sudden death at the hands of Madeline in Part 7 is shockingly heartwrenching, to the point where even Joel was broken by it.
- Garfield calls Bogan's phone to hang out after his soul is reaped to see if it will somehow glitch him back to life. The response?"Bulk is sleeping."
- Pepsiman is completely distraught over Fren's almost immediate death and calls out to him as he's being butchered before mourning his death.
- Funky Kong's equally sudden death in Part 9. He walks outside of his home before being run over by a car out of nowhere, shocking Joel and the chat, causing him to let out a Rapid-Fire "No!". Bonzi leaves from work early to plead with the Reaper, which seems to succeed at first, but doesn't. Thankfully, Funky came back as a ghost and Bonzi used his magic to revive him later on.
- Dio being harassed and then brutally beaten up by two Sims at the climax of Episode 10. Doubles up as a moment of funny for how it comes out of left field, and an awesome moment in how Dio quickly recovers to take the both of them out, but afterwards its quite clear hes been messed up quite a bit by it, as evidenced by his emotions changing to Very Sad. Given that in this series, Dio tends to be quite sentimental and tearful at the most unexpected times, considering what just happened makes this moment a bit more heartbreaking.
- Part 11, the intended first season finale, opened with a bang as Jill and Nemesis tried for a baby. Immediately after, Nemesis was run over by a taxi and killed before Joel could plead for him, and Jill was revealed to be pregnant shortly after. Jill and Wesker's "Very Sad" moodlets reflected Joel and the chat's sadness over the matter, especially since Joel revealed his original plan was for them to marry.
- Despite a 90% success rate for fixing a gunshot wound and an attempt to become a vampire, Spongebob failed to be cured, and his roommates and ghosts mourned him. He dropped dead right in front of Johnny Zest's house, and Wesker's pleas fell on deaf ears. Making it worse is that Spongbob took the bullet for Wesker.
- When Jill's baby was finally born in part 11, it was taken away immediately. This and the previous events were so distressing that when the save file was accidentally reset, Joel declared it a noncanon What If? episode and said the real finale would take place another day.
- Johnny finally breaking down in Part 12. The combined stress of having a wedding forcibly taking place at his house, a majority of the guests there being people who tormented him and having to shoot an armed burglar in self-defense causes him to snap, donning clown makeup and dying his hair to become Dark Johnny then going on a crotch-kicking rampage, which does not exclude his best friend Twitch Chat.
- The rampage ends when he finds himself unable to confront Bulk, arguably the sim Johnny loathes the most, because Bulk is too strong. Johnny starts sobbing, and Joel adds that by the end of it Johnny feels regret for his actions.
- Nathan (one of the two cops who frequently appeared) dies from one of the demons Doomguy battles in Part 12. It's a very sudden and out of the way death of a minor character but gets sad when remembering that he's been there for several classic moments. That and his buddy will now be alone...
Tear Jerker / Meme House