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- 3 December - Chris reaches out to The Sergeant at Arms requesting inclusion of his fanmade Sonichu Villains cards into Chris's own TSSSF line.
- 7 December - Chris, triggered over ProjectSNT's fanart redesigns of the Chaotic Combo and sick with a UTI, bitches on Twitter about it, tweeting in Yoda-style word salads.
- 8 December - Chris live-streams himself taking photos of the TSSSF cards.
- 10-11 December - In The Place, Chris, still getting over a cold, complains about ProjectSNT's redesign of Wild Sonichu. Watchmen members take Chris's side and criticize the redesign while encouraging Chris to look into another dimension to figure out the issue and make peace with it. The Watchmen also propose to Chris the creation of a dating sim game.
- 14 December - In The Place, Chris discusses his thoughts on ProjectSNT. He describes having sent her an angry email, which he claims remorse for, and that he had sent a subsequent email apologizing. He mentions that he is tense over her lack of response, then manipulates the Watchmen into sending her an email on his behalf, which ProjectSNT also ignores.
- 15 December
- The first of the known AquaDiamond8 DMs, in which Chris described his fantasy adventures with Val and how to remember "conduit".
- Chris asks for Jacob Sockness to be kicked from the Watchmen's server The Place.
- Chris has a dream about his transgender self being pursued as a love interest by his past self.
- 19 December - Chris continues monitoring ProjectSNT's social media and is "mildly ticked" to find she has continued to ignore him. He asks Watchmen if she has responded to any of their messages and is told she has not. The Watchmen also advise against further messages.
- 23 December
- 25 December - C-Mas.
- 26 December - The 5-year anniversary of the GameStop macing incident.
- 28 December - Reddit user /u/mkicon encounters Chris in Tetris 99 a second time, having earlier encountered him in July.
- 30 December - TheGamerFromMars meets up with Chris.
- AquaDiamond8 DMs
- CWCville (Discord server)
- Dillin Thomas DMs
- The Place chats (December 2019)
- The Sergeant at Arms e-mail and DMs
- The Sergeant at Arms
- Twilight Sparkle's Secret Shipfic Folder Livestreams#Taking TSSSF Product Photos
- The Place chats - ProjectSNT and Opuscon789#Cold, ProjectSNT, and Dating Sim
- The Place chats - ProjectSNT
- AquaDiamond8 DMs
- The Place chats - Jacob Sockness#Chris asks for Jacob to be kicked
- The Place chats (December 2019)#Two Chrises dream
- The Place chats - ProjectSNT#More Seething Towards SNT
- The Place chats - Jacob Sockness#Marvin blocks Sockness, fated Pokemon card
- Tetris 99#28 December 2019