Dan Cereill (pronounced “surreal”, NOT “cereal”) is not having an easy time of it. He and his mother are left shocked, abandoned and nearly penniless after Dan’s father simultaneously announces that his business has gone bankrupt and that he’s gay. Dan’s great-aunt Adelaide recently passed away, the terms of her will stating that Dan and his mother could live in her house (although the house and it’s contents were left to the National Trust). The house is ancient, drafty, cold as hell and reeks overwhelmingly of urine, but Dan can cope because it’s also next door to his dream girl, Estelle. By accident, he discovers that the two houses have connecting attics, and Estelle has made herself a sort of refuge up on her side. Lonely, miserable and conflicted, Dan can help himself from snooping through Estelle’s private things, including her notebooks and diaries, seeing how much they have in common.
He makes a list of six impossible things he hopes to achieve, the most important of which is that he wants to kiss Estelle. Of course, he gets completely tongue-tied and awkward talking to ANY girl. Estelle is so far out of his league it’s not even funny, and he’s deeply ashamed about the fact that he snooped through her diary, betraying her trust before they’d even properly met. His parents’ sudden financial difficulties means his mother is trying to make money by starting a wedding cake business. She doesn’t really sell any wedding cakes, instead more often than not breaking the couples up after their consultations with her. Dan therefore needs to get a job, in an attempt to help out with bills.
He also has to leave his fancy prep school and get used to going to public school, where he manages to make himself a target for bullies on his very first day. He struggles to make friends, admiring Estelle and her friends from afar, cursing his bad luck and painful lack of cool or social skills.
While Dan reading Estelle’s diaries early on is a very bad thing to do, he clearly feels extremely bad about it, and he’s in a very bad place emotionally when he succumbs to the temptation. So while it can seem a bit stalkery and inappropriate, he is very sorry and tries not to do it again (too much). He’s adorably clueless about girls, and extremely annoyed that his reputation as a prep school kid marks him out as some sort of sad nerd. When he befriends Lou, who seems to be the female flipside of his best friend Fred, it’s clear that his penchant for saying exactly the wrong thing to Estelle has more to do with nerves and anxiety than anything else.
Dan feels very betrayed about his father’s revelations and feels abandoned by him. He stubbornly refuses to speak to his dad at all, or open the birthday present his dad sends him. He tries as best he can to help his mother, who is very effective at breaking up affianced couples, but not really in securing a single client for her baking business. When she’s not making brides reconsider marriage, she mainly mopes around, obsessing about Radiohead. Money is clearly very tight, which becomes more of a problem when Howard, the elderly dog Adelaide left them needs some serious vet’s attention. Dan manages to get a part-time job, but discovers that a 15-year-old waiter doesn’t exactly make a fortune.
Going for runs with Howard and lifting weights in his room, not to mention some advice from Oliver, the cool market analyst who lives in the mansion’s carriage house, means Dan slowly builds both muscle and confidence and as the school year progresses, he starts fitting in better at school. The bullies mainly leave him alone, and as he works in the same café as Janie, Estelle’s best friend, he is eventually roped in to help in a harebrained scheme to get Janie to Sydney without their parents discovering. While their parents discover their deception and Estelle and Janie end up grounded for ages, it means he’s finally earned the trust of the girl he adores. She uses their shared access to sneak into Dan’s house and they spend a lot more time together.
By the time the big dance comes around, Dan is going mad with jealousy because he knows Estelle is taking someone else. When he discovers she’s going with a girl from a different school, he finally summons up the courage to show her how he really feels. His guilty conscience about killing her diaries is nearly killing him, though. Will he ruin all his chances with Estelle just as he’s finally managed to get her to really see him as a romantic prospect?