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Jacklyn's Naughty No Trick, All Treat, 31 Days of Halloween Contest was a contest Jackie made for Chris, where he would have to make a new cosplay video for every day of October 2010, and/or share at least one fact about himself and/or his life. Chris would initially refuse to do it, which made her cry, but he would become completely on board after a few rule clarifications. Jackie also clarified that if he succeeded, she would have sex with him. This contest resulted in a huge amount of videos uploaded that month, a quantity has yet to be topped by Chris ever since. It also, barring one more video uploaded the next month, serves as the last hurrah of the 'classic Chris' era, prior to him coming out as a tomgirl. Jackie came up with the idea immediately after Chris posted Song for Jackie.MOV, possibly seeing the gold mine of content that could come from Chris cosplaying.

Most of Chris's cosplays are completely bizarre depictions of the characters, that no-one would be able to recognize if not told who it was by Chris. Also, while the intent was for Chris to upload a video every day of the month, Chris would often be late and upload videos days later, citing his computer and Internet issues as the result - though other times, he would claim he would upload videos using the Internet at the Alderman Library, but then forget to do so for weeks. Chris also half-assed a lot of the videos made for the contest due to laziness, or having discomfort or unwillingness to do the task he was given (such as rewriting the ending to Sonichu 10 to show forgiveness towards Alec Benson Leary and his crew, or simply cleaning his dirty shower); this was despite the potential reward for properly following the rules being him finally no longer being a virgin with rage. Ultimately, the contest ended with Jackie being too frustrated at Chris to give him some china.

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