September is the ninth month of 2019.
- 6 September - Barb takes the Dodge Caravan for repairs and is told the brake and exhaust systems need to be replaced for $1,000. Chris begs for the money, asking fans to give the money through business associate Jacob Sockness.
- 7 September - Jacob Sockness forges a conversation between himself and Magi-Chan on Reddit, asserting that he and Chris must meet in person and marry for the Dimensional Merge to take place. Chris affirms through his Magi-Chan sockpuppet that the dialogue is authentic.
- 10 September - On Twitter, Chris (via Magi-Chan) laments the loss of his friends in the Teen Troon Squad and expresses his wish to meet them again in person, casually providing two more of their names in the process. He also alleges that Magi-chan's body (piloted by Chris's soul) has arrived in California, yet Chris's own body remains safely in Ruckersville.
- 13 September - While telling a brony on Twitter to believe his own fursona is a real, independent being, Magi-Chan describes Borb as being his waifu, with Chris's mother in particular being his "Guilty Pleasure".
- 14 September - After a month spent pretending to have swapped bodies with a fictional character, Chris returns to his normal Twitter account. He describes his fabulous adventures with Sockness in California, noting that he expects him soon to visit Virginia.
- 22 September - In a dialogue on Discord, Chris admits that he drew artwork that he had attributed before to Magi-Chan.
- 23 September - A full decade passes since the last time Chris applied for a job.
- 25 September - Sockness proclaims on Reddit that he has secured transport to visit Chris in person.
- 25-26 September - Chris releases multiple statements asking Jacob to turn around, saying among other things that his health is not well for visitors, and that Jacob has turned to evil.
- 27 September - Jacob Sockness quarrels with Chris and reverses course, retreating to his home in California instead of continuing to meet Chris in person.
- 28 September - On Twitter, Chris states his wish to attend BABSCon, a brony convention in California scheduled for April 2020, and bids his followers finance his trip.