- Jerkass Woobie: Lori. Early scenes show her engaging in a mean, racist prank, and she cheats on Skippy, breaking his heart. But she's also engaged in a somewhat abusive "relationship" with Carl that mostly involves exchanging sex for drugs (which she wants because of her insecurity about her body), and you can't help but feel for her when he films her questionable-consenting blowjob and sends it out to the whole school, and she panics, thinking she's pregnant. The last section of the book reveals her to be desperate for love and with few real friends, which drives her to suicide.
- Rewatch Bonus: The more you reread the book, the better you understand what's going on. For example, you start to recognize the ton of Foreshadowing that Skippy was molested by his swimming coach. And you start picking up on all the Harsher in Hindsight moments.
- The Woobie: Skippy. He's a sweet, innocent, Adorkable kid who is the center of his friend group. The first two thirds of the book detail his life getting destroyed under a gauntlet of assaults: getting bullied at school, dealing with his mom's slow death, having his heart broken in a shocking way, being raped by his swim coach, and becoming addicted to drugs to cope with it all... And then he dies at the age of 14. Heartbreaking.
YMMV / Skippy Dies