The Boy Book by E. Lockhart
Ruby Oliver is quirky, funny, totally neurotic, has quirky parents, and lives on a houseboat. She wears fish nets and combat boots. In many ways she reminds me of me when I was in high school. In this second book in the series, Ruby is returning to school at the end of summer and is still a social leper. Her best friends have abandoned her, one of whom is dating her ex boyfriend, Jackson, who she may or may not still have feelings for.