April 2011 consisted mainly of Chris continuing to play PS3 and hiding from trolls. He also renewed his relationship with Jackie. At the end of the month, the PSN suffered a worldwide security breach, which led to Chris's account being hacked again. Shortly thereafter, a bunch of pictures wherein Chris dresses like a woman in public surfaced on the internet. It was hotly debated whether this meant that Chris was coming out of the closet, or whether it was another plan pertaining to his Love Quest.
- 14 April - Encyclopedia Dramatica, the website that made Chris infamous, is taken down and replaced with "Oh Internet." Chris finally got his wish.
- 16 April - It does not last long however, as a semi-complete mirror of Encyclopedia Dramatica, including the Chris-chan page, is established.
- 18 April - Jackie decides to finally respond to Chris's email of 26 March, writing that she was turned on by his tomgirl photos and wants more.
- 21 April - Chris replies to Jackie, telling her to keep his tomgirl photos private, and inviting her to Charlottesville for sex, assuring her that he still has a penis.
- 21 April - Jackie replies that Lars is out of the picture, but that she wants to take it slow with Chris.
- 21 April - Chris agrees to take it slow with Jackie, but says that they should talk on the phone twice a week, and that they should meet and have sex by mid-May. He also says his mother is criticizing his new look.
- 21 April - PlayStation Network shuts down after an "external-intrusion" by hackers, rendering Chris's PS3 unable to connect to the internet and impulse-buy large amounts of vidya.
- 22 April - Jackie reiterates that she wants to take it slow with Chris.
- 23 April - Chris tells Jackie he's made up with his mother, and that his father has recently had cancer surgery.
- 24 April - Chris sends another email to Jackie, discussing makeup, laptop computers, and his physical revulsion at seeing dicks.
- 25 April - Jackie asks Chris about the Game Place and fashion.
- 26 April - Chris shares with Jackie more details about tomgirlism. He fantasizes about seducing and scissoring with a lesbian, not for the last time.
- 26 April - Jackie replies by sharing her own fantasy involving gay sex.
- 28 April - Chris tells Jackie that he can tolerate her fantasy.
- 29 April - Several pictures of Chris dressed as a woman are released.
- 30 April - Chris discovers the leaked photos on the CWCki and tells Jackie. He is shocked.