- Shoto slowly and painfully explaining his relationship with Daito and the events of his death.
- In the trailer quite a few people look absolutely heartbroken to hear about Halliday's death.
- Although it's part of Wade's plan, his time as an indentured servant to IOI is absolutely soul-sapping and depressing. Also serves as Nightmare Fuel implying this is what will become of the world should IOI win the Egg Hunt.
- After Sorrento essentially destroys Wade's home and kills the people inside in the process, Wade mourns (not for his Aunt Alice or her boyfriend) but for his sweet neighbor Ms. Gilmore.
- Sorrento and the sixers gaining the crystal key becomes a Despair Event Horizon to Wade and the entire Gunter community.
- This also marks Wade's Darkest Hour. He's about to lose the virtual world he grew up in to an evil corporation, he can't talk to Aech (because of their recent falling out), can't talk to Art3mis (because of their break up, and she won't be in a happy mood), and his AI butler Max can only offer so many comforting words before he repeats himself. If Shoto hadn't asked to visit Parzival, Wade would've likely gone through with selling his virtual belongings, terminating his OASIS avatar, then terminating himself.
- To add insult to injury, it's not long before we learn Daito was killed in both the OASIS and the real world.
- Art3mis breaking up with Wade. The latter is 100% convinced he unconditionally loves her no matter what she looks like, but she doesn't believe he does and cuts off all ties with him.
- An excert in Chapter 19 where Wade sadly comes to the realization that immersing himself in the OASIS is a form of "self-imprisonment", and how inadequate it is to stave off his loneliness after Art3mis breaks up with him.
- Bordering on Fridge Horror, Art3mis (or rather Samantha) being so cripplingly self-conscious about her port-wine stain in the real world that she treats it as a secret deformity in the OASIS.
- It is obvious Ogden misses his good friend James and his wife Kyra, even so long since they both died.
- From the film: "Thank you for playing my game."
- Two moments from the film, featuring Ogden Morrow: Og's voice cracking when Wade tells him he's splitting the fortune and rights to the Oasis with his clan as Og tells him "that's a good choice." And then again moments later, the look on Og's face when Wade tells him he was Halliday's best friend and 'Rosebud' is enough to make anyone cry.
Tearjerker / Ready Player One