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May was the fifth month of 2011, beginning just after a series of photos of Chris in women's clothing was leaked. Publicly, Chris remained inactive, but corresponded regularly with Jackie and other trolls; he also joined the Tomboys And Tomgirls of Virginia forum.
- 1 May - Jackie suggests to Chris that the leak of his private photos might have been due to the recent hack of PlayStation Network.
- 2 May - Chris accuses Jackie of leaking the photos.
- 3 May - Jackie angrily denies Chris's claims. Chris tells her he needs to think about her statements.
- 4 May - Chris's parents yell at him about dressing like a woman.
- 5 May - Chris apologizes to Jackie, and tells her about the friction with his parents.
- 5 May - Chris writes a "press release" about his being trolled.
- 6 May - Chris gives the press release to Jackie, hoping she can publish it.
- 7 May - Chris and Jackie argue about money, the internet, and trust.
- 8 May - Chris tells Jackie he feels paranoid and confused, and that he wants to see her in person.
- 8 May - Jackie tries to make Chris aware of his hypocrisy and dishonesty.
- 10 May - Chris responds to Jackie but fails to address her concerns.
- 11 May - Chris reiterates to Jackie that he wants to meet her soon.
- 12 May - Chris reflects on his past mistakes with Jackie, internet fame, and real-life socialization.
- 13 May - As an experiment, Jackie sends Chris a deeply sarcastic email, to see how much he picks up on.
- 14 May - Chris misses the sarcasm, but defends himself against Jackie's claims. He says he feels trapped by his family situation.
- 14 May - After almost a month of being inactive, the PlayStation Network comes back online, and Chris immediately removes the "I am Tomgirl" quote from his profile.
- 15 May - Chris shares with Jackie more information about his parents, his comics, and his feelings about Osama ben Laden.
- 16 May - Jackie pushes Chris to make more comics, find a job, and learn about his tugboat.
- 17 May - Chris tells Jackie that Barb threatened to kill him, and then cut his hair. He called her a bitch and tried to magically induce his hair to grow back.
- 18 May - Jackie continues to aggressively confront Chris about his life choices.
- 19 May - Chris ignores all of Jackie's points. He tells her he is wearing a wig for the time being. He also mentions that he has asked Rocky for help in moving out of his house and "into a place based on my Autism."
- 21 May - Chris shares with Jackie some sketchy details about the plan for him to get autism-related housing and assistance. Jackie tells Chris to take control of his life.
- 24 May - Jackie asks Chris how he's doing. He replies with a blank email.
- 25 May - Jackie apologizes to Chris for constantly carping at him.
- 26 May - Chris tells Jackie he's learned about a forum that's relevant to his interests.
- 28 May - Jackie sends Chris another sarcastic email criticizing him for his inaction. She says she's too busy to meet him in person.
- 29 May - Chris did not get Jackie's last email, and says he's doing well.
- 29 May - Chris joins the Tomboys and Tomgirls of Virginia forum. It is revealed that Bob called him a "fag" and Barb said "I didn't raise a daughter," and Chris recounts a confrontation with a jerkop.
- 31 May - Chris tells Jackie he has new gal-pals, but they're all waitresses and retail store employees. He shares some details about his half-brother Cole.