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.
- 14 May - Mary Lee Walsh retires as PVCC's Dean of Student Affairs.
- 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.
- 26 May - Sarah and Steve bail on Chris, posting that they had been swindled out of hundreds and treated as subhumans.
- 30 May - Chris tweets about Mary Lee Walsh's retirement. He claims to have reconciled with her, but still complains about her conduct in 2003 and asks whether she made any statement regarding his previous apologies.
- Chris vs. Portfolio Recovery Associates, 2019 (GV19000149-00)