The things described in this article are still happening, so it may be subject to frequent change.
May is the fifth month of 2019.
- 1 May - With the release of the first trailer, Chris voices his discontent with the Sonic the Hedgehog movie.
- 6 May - Chris is sued for debt for the fifth time. The creditor this time is Portfolio Recovery Associates, LLC, filing its second debt suit against Chris.
- 9 May - Chris sees the Detective Pikachu movie. He gives it a glowing review.
- 11 May - Chris dumps a bunch of retconned lore about Reldnahc Notsew Naitsirhc on Twitter.
- 13 May - Chris lists a throw blanket on eBay for $200, tweeting: "we need the money here, that’s for sure. Thank you." Jacob Sockness buys it the next day.
- 15 May - The first court hearing for the April 2019 warrant in debt for money owed to Portfolio Recovery Associates takes place: the case is adjourned to 19 June, when it will be heard in conjunction with the May 2019 warrant in debt.
- 21-22 May - Sets of Twitter DMs from the latest people trying to worm their way into Chris's life, Sarah and Steve, is posted.
- 24 May - Midland Funding files for garnishment against Chris after he failed to maintain payments on a $2,777.90 judgement from December 2018. The Sonic the Hedgehog movie is announced to be delayed to 14 February 2020.
- 25 May - Chris goes on a tweetstorm over his sleeping methods. He is also interviewed by Youtuber Nick Robinson over his rumored discovery of Pappy Van Poodle, a character from Rusty's Real Deal Baseball.
- Chris vs. Portfolio Recovery Associates, 2019 (GV19000149-00)