I read this book in middle school about this teenage girl-boy romance. The girl was popular and the boy was not. He was also obsessed with birds throughout the entire novel. The girl had a younger sibling who she kept getting separated from, because of her parent’s divorce. She basically had a really bad home life and a lot of mental health issues. It was making her suicidal and super erratic. There’s one chapter where the girl strips in front of the boy during their first date. The boy was definitely the main character and I can’t remember if they ended up together. This story was old, definitely before 2000.
Lost Classics of Teen Lit: Name That Book! 