May was the fifth month of 2021. Chris uploaded a video of himself covering the song "I'll Be Your Mirror" by The Velvet Underground this month, and uploaded a bizarre audio clip to Twitter in which he vocalized his voice. Aside from this, Barb's debt hearing was continued to July 2021.
- 4 May - Chris releases a seductive image of Chris-chan Sonichu on social media.
- 9 May - Chris celebrates Mother's Day.
- 11 May - Chris resumes messaging Sean Walker on Discord.
- 17 May - Chris gets his second dose of the Pfizer COVID-19 vaccination.
- 19 May - Barb's debt hearing is continued to 14 July 2021.
- 19 May - Chris announces on social media that he and Barb have been given COVID-19 vaccinations.
- 20 May - Chris releases a new photo of a Sonichu medallion on Instagram, stating that he had just applied "a fresh bit of paint and epoxy covering."
- 20 May - Chris releases a bizarre audio clip of him vocalizing on Twitter.
- 26 May - Chris shows off a book on social media about comparing himself and Andy Warhol.
- 26 May - Chris posts a bizzare series of tweets ranting about his failed relationships and trolls.
- 27 May - Chris uploads a video of himself covering the song "I'll Be Your Mirror" by The Velvet Underground.
- 29 May - Chris announces that the prices of the meditation crystals and enchanted rocks on Praetor's Etsy shop are lowered from $45 to $20.
- 31 May - Don Lashomb, author of Warhol / Chris Chan, is interviewed over Reddit by a CWCki editor.