- By far, one of most heartwrenching things about the game is that you can never respond to anyone. You can never tell Mr. Smiley that his presents make you happy. You can never tell Salvadore that you're alive and you got his presents. You can never tell Charlotte that you're going to see her.
- Anytime Mr. Smiley breaks his happy, exaggerated attitude and sends you short letters merely saying "I'M SORRY" or him literally begging you to be happy.
- As the days progress, Mr. Smiley becomes so desperate to make you happy that he spends all his money to buy you a new game. Then he sells one of his organs to get more money to buy you another game you don't need.
- Salvadore expressing how happy he'll be to return to his hometown. When he comes home, he finds out that everyone's either dead or gone.
- Day 5 is filled with sorrowful moments guaranteed to make the players weep.
- Charlotte's suicide. She sends you a letter saying "I'm sorry." With blood staining the letter. Everything leading up to it just makes it much worse, since you know it's coming.
- Salvadore's Heroic Sacrifice. This happens after Charlotte kills herself, and to add icing to the cake, Dr. Money taunts you about his death.
- Finding out about Mr. Smiley's backstory. He was forced to be your Happy Buddy because Dr. Money kidnapped his daughters. He then reveals to you that they recently died and he never got to say goodbye. Mr. Smiley, having lost all hope, decides to sell all of his organs for money, knowing he'll die. He then tells you, with no emotion whatsoever, "Goodbye," and you never hear from him again.
- The ending. Even if you leave the cell, you walk outside the building and find Charlotte's bakery, with blood everywhere and a suicide note. While the game does end on a somewhat bright note, it doesn't change the fact that the only three people you've been talking to (excluding Dr. Money), are now dead. And it's heavily implied that you're one of the last survivors on the entire planet.
- The game's creator, Wertpol, had planned on eventually revamping the game and its companion title, but tragically committed suicide in 2018.
Tear Jerker / Presentable Liberty