—Chris, calling out the Idea Guys.
May is the fifth month of 2018.
- 1 May - Chris gets mad on Facebook, blocking two people for making fun of him and correcting another for deadnaming him.
- 2 May - Chris whines about his Patreon backers reducing their pledges and offers an extra Sonichu license plate on eBay.
- 4 May - Chris uploads Beedee, Beedee, Beedee; I’m Back, Buck! to apologize for the lack of progress on Sonichu and announces an exclusive comic to his Patreon backers featuring himself, Magi-Chan and Cryzel Rosechu. He also begs for sales money, allegedly to afford shipping out books, even though he had gotten $450 from Patreon donors two days prior and made thousands of dollars from eBay sales/gifts in the previous month. Finally, after Kenneth Erwin Englehardt had enough of Chris's rudeness and walked away from his Facebook, he quickly backpedals, tweeting to Chris instead.
- 5 May - Chris confirms that his recent sweethearts are Cryzel and Magi-Chan when he uploads a preview of a special wedding story for Sonichu #16. He puts out an ambiguous statement that something bad happened to him during the last six months and that, as a result, his finances are the worst they've ever been.
- 7 May - Upset at how he was banned from Anytime Fitness, Chris turns his back on the CWCProtectSquad.
- 8 May - Barb and Chris beg in multiple videos for mortgage payment money, saying they must pay tomorrow and are at risk of foreclosure if they do not, and Chris states that something happened to him over the last six months which caused him to lose a lot of money. He slashes prices on eBay and offers a celebrity visit from himself for $500. He also continues his court visit for the Trespass After Forbidden charge, ending with a continuance issued for 5 June.
- 9 May - Chris scrounges up the money to make the mortgage payment and blames the mortgage company for being "money-gouging assholes".
- 10 May - Chris has a temper tantrum on Twitter and video. Barb appears in two paid request videos.
- 13 May - For Mother's Day, Chris makes two drawings of himself holding hands with his CWCville counterpart, saying that he is her mother. He notes that the CWCville Christine is touching his butt.
- 15 May - Chris changes his Facebook status to say that he is married and comments that it is to Cryzel and Magi-Chan, saying it's fine because he's half-Pokémon. He unmasks LittleAmychan, posting a video she had sent him privately over suspicion that she is a troll. He tries to guilt his patrons into raising money for him to get the books they already paid for shipped faster.
- 16 May - Chris calls out Michael Hirtes over his constant weening.
- 17 May - Chris posts that Sorbet has gone missing for the past week.
- 19 May - Chris explains why he carries a baseball bat around town.
- 20 May - Chris posts that Pollo has died due to natural causes.
- 23 May - Chris uploads a preview for new pages of Sonichu 12-9. Later, he thanks people who gave him donations, noting for his audience that he was given Food Lion gift cards as a way of ensuring he would only spend the donation on food, and that he's still in financial distress. He sets standards for the video requests he'll make, specifically no more shout-outs to school shooters and donated food he'll eat, turning down an offer for pizza as it's junk food. He puts a price tag of $1,000 on his Twitter account to a fan who asks about buying it.
- 24 May - Chris calls out the Idea Guys and disavows some of their content. He roasts Kenneth Englehardt on Twitter.
- 25 May - Chris hesitates on publishing Sonichu #16, as it was co-authored by Idea Guy. He tweets he's still in need of food money, suggesting that if people want to be sure the money goes to food, they can send him Food Lion gift cards, and offers to show receipts to show it won't be wasted on junk. He also says he is exploring ideas to level off his financial situation, but follows up by saying, "And NO, don't tell me to 'Get A Job' - you know I would be Harassed until the End of Equestria! I Prefer to Work From the Peace of my Own Home". A fan suggests he simply not tell people where he would be working, but Chris responds that this wouldn't be enough, saying, "They would Find Out. Lots of people in CVille know who I am - Someone would See Me Working and it would be Online within Minutes!"
- 26 May - Chris hangs out with Copitz, one of his fans.
- 29 May - Chris gives a "frowngrade" to the DuckTales reboot. He rejects drawing advice on not using a pen for line art.
- 30 May - Chris draws art in appreciation for Joshua Moon, the owner of Kiwi Farms. Copitz releases a video of him and his friend chatting with Chris, filmed a few days prior.
Kun T'Nyuget meets Nightstar, Sonichu 12-9
A drawing for Joshua Moon / Null, owner of Kiwi Farms.
- Beedee, Beedee, Beedee; I’m Back, Buck!
- WE NEED MONEY FOR MORTGAGE NOW, PLEASE
- SERIOUSLY, BUY THE TOYS FROM ME NOW, PLEASE!
- Please, HELP US! FORECLOSURE RISK HIGH!
- May 2018 Paid Video Requests
- I Am Sick of the HATE!!! (I could use a break)
- Chat with Copitz
-  and