February 15, 1992
Charlie and Mary Elizabeth go on their first date at the Sadie Hawkins dance, and Charlie learns a lot about Mary Elizabeth's hopes, dreams, future plans, and complaints. She talks for almost the entire time, but at the end of the date she tells Charlie that he is the most sensitive boy she has every met. It also turns out that Sam and Craig had a big fight because Craig decided not to go to the dance. After Charlie drops Mary Elizabeth off at her house, he finds his sister crying in the basement. He tries to talk to her and make her feel better, but these efforts only result in her yelling, "CHARLIE! SHUT UP! OKAY?! JUST SHUT UP!" (274) She starts crying even harder, and she eventually tells him that she is pregnant. She had tried to tell her boyfriend, but he had denied that it was his baby and broke up with her right at the dance. His sister does not want anyone else to know about the baby, and this becomes another secret that brings Charlie closer to yet another individual.
February 23, 1992
Charlie drives his sister to the abortion clinic and sits in the waiting room while she goes through her procedure. He decides to sit in the car because he is about to start crying and does not want anyone to see him break down. While he is sitting in the car, he thinks about all of the times his sister has changed - how she became a young lady and how she began to realize she is pretty - and he wonders about how the abortion will change her. His sister leaves the clinic and finds Charlie smoking, and she threatens to tell their parents. They both know that this will never happen, and they start laughing. Charlie can't stop laughing the entire way home. They return home and tell their parents that they have been at a movie for the afternoon, and at the end of the evening Charlie's sister thanks him for everything that he did. They tell each other they love each other - a rarity in their relationship.
March 7, 1992
Charlie's relationship with Mary Elizabeth has begun to progress, and Charlie's sister tells his parents that Charlie has a girlfriend. When he asks for the car so he can pick Mary Elizabeth up, his father comes upstairs and talks to him about sex and asking for consent before doing anything. The most recent date ends with the new couple in Mary Elizabeth's house drinking brandy, the only thing she claims that she likes as much as her parents like; after a while, Mary Elizabeth begins moving closer to Charlie. Things move quickly and they do "everything you can do from the stomach up," stopping just before Mary Elizabeth's parents arrive home(299).
March 28, 1992
The weather is getting nicer and people feeling better, but Charlie is having a difficult time with his relationship with Mary Elizabeth. They will talk for entire days, and then as soon as Charlie arrives home, Mary Elizabeth will call and ask, "What's up?" even though they haven't been apart for long (303). Charlie is disappointed that Mary Elizabeth invited herself to the special dinner he was going to have with Sam and Patrick at his house; at this event, his parents only focus on getting to know Mary Elizabeth. Charlie doesn't know what to do even though he wants to break up with Mary Elizabeth. His sister tells him to just be honest.
April 18, 1992
All of Charlie's frustration over Mary Elizabeth has erupted and "made a terrible mess of things" (312). During a game of truth or dare, Patrick dares Charlie to kiss the prettiest girl in the room on the lips, and Charlie decides that he is finally going to be honest - so he gets up and kisses Sam. Everyone is shocked, and Mary Elizabeth storms out. Sam follows her, and Patrick escorts Charlie out of the room. He drives Charlie home and encourages him to stay away for awhile. Charlie is distraught and disappointed with himself. All he can say is, "Something really is wrong with me. And I don't know what it is" (325).
April 26, 1992
Nobody has called Charlie since the kiss. He has called Mary Elizabeth several times to apologize, but all she has said is, "It's too late" (326). Easter has passed, but Charlie doesn't say much about it because his experiences with this holiday were similar to his experiences at Thanksgiving and Christmas. Charlie wants his friends back. He wants to find a way to erase what happened. He writes somewhat desperately, "I just wish that God or my parents or Sam or my sister or someone would just tell me what's wrong with me. Just tell me how to be different in a way that makes sense. To make this all go away. And disappear" (329). Charlie has been smoking a lot of pot in an effort to feel better, but this activity doesn't seem to help much.
April 29, 1992
Charlie has reverted back to his position as an observer. He has been walking around the hallways of his school trying to learn more about the people who are with him, and he has also been going to the mall alone, just to observe. Things that Charlie used to do by himself now make him feel lonely because he knows how happy he is when he is with his friends. The only person he has talked to since everything imploded is Susan, the girl who used to "go with" Michael, but she only stares at Charlie blankly, offering no response. As he walks away from his attempted interaction, another kid whispers, "God, that kid is such a fucking freak" (340).
Once again, secrets enter Charlie's life. When he finds his sister has had an unplanned pregnancy, the themes of sex and secrecy collide. His sister's unhealthy relationship falls apart when she tells her boyfriend that she is pregnant. The immediate end of the relationship shows that sex, not emotional support, is what ties the boyfriend to Charlie's sister. While not as blatant as the sexual abuse that has been discussed in earlier portions of the book, this form of unpleasant sexuality is another distortion of the beauty and love that should go along with sex.
For his part, Charlie has been seeking a close relationship with his sister, yet hasn't been able to find it. Now that he has access to her biggest secret, they are drawn closer together. Despite the severity of the situation overall, Charlie and his sister are able to find lighter moments and laugh with one another. Their mother and father are oblivious to all that has just occurred, but are happy to see that their children have been spending time together.
Charlie's reaction to the pregnancy and the abortion showcase his tendency to observe rather than to speak up. Charlie has no questions to ask his sister; he just sits back and listens. He wants to comfort her, but he has no idea how to offer meaningful questions or suggestions. He can only listen to her and give her a shoulder to cry on - a repeating trend in Charlie's interactions with others.
When Charlie does muster the strength to speak up and say something, he finds it difficult to be honest. His relationship with Mary Elizabeth is progressing rapidly, and she has begun to annoy him. Eventually, Charlie finds himself asking everyone for advice, and everyone tells him different versions of the same thing: be honest about your feelings and break up with Mary Elizabeth. When Charlie finally decides to be honest, he chooses the worst possible setting. His decision to kiss Sam is both an attempt at honesty and an instance of self-interest. He is tired of hearing about Craig, and he wants to become closer to Sam. In the moment, he does not realize the damage he will do.
Without his friends, Charlie deteriorates. He begins to lean on substances like pot and alcohol, and his writing mirrors his unstable mental state. He is aware of how difficult his life has become without his friends, and his regression becomes especially apparent when he reverts to activities he once pursued by himself. Now, these pursuits are not nearly as fun because he knows how much fun is possible with his friends. Once again, his friends are clearly the scaffolding to the success of his life.