The story follows a (school) year in the life of high schoolers and best friends Halley Cooke and Scarlett Thomas. Scarlett is bold, brash, and popular; Halley is far more reserved, notable only for her association with Scarlett. Then, Scarlett's boyfriend is killed in a motorcycle accident— and shortly after, Scarlett discovers that she is pregnant. For the first time in her life, Halley must step up and be Scarlett's support system, which becomes more difficult once Halley starts dating resident bad boy Macon Faulkner.
The 2003 film How to Deal is adapted from both this novel and Dessen's previous one, That Summer.
This novel contains examples of:
- All Girls Want Bad Boys: Halley for Macon.
- Amazingly Embarrassing Parents: Halley's father is a DJ at a local radio station, where he tells humiliating stories about Halley that her school hears. Not to mention her mother publishes books about her and Halley's relationship. It's a large factor in why their relationship is so precarious.
- Armour-Piercing Question: Halley ends up in the hospital because of Macon's bad driving. When he shows up at Halley's house, she promptly breaks up with him, not only for that but also constantly pressuring her to have sex with him. When she goes back inside, her mother immediately starts yelling at her, telling Halley she won't let her ruin her life because of Macon and threatens to transfer her to another school. Halley interrupts her with, "Why don't you ask me what I said to him?"
- Betty and Veronica: Noah (Betty) and Macon (Veronica) for Halley. Subverted that Halley isn't at all interested in Noah and ends up breaking up with Macon. Halley later becomes the Betty when Macon begins dating Elizabeth Gunderson.
- Can't Get Away with Nuthin': Scarlett and Michael have sex once. Not only does Scarlett get pregnant from the encounter but Michael dies the next day.
- Daddy's Girl: Somewhat zigzagged with Halley—she initially was very close to her mother but as she grew into a teenager and started drifting apart, her mother becomes more controlling, so Halley finds her father easier to deal with.
- Good Girls Avoid Abortion: Scarlett is pressured to have an abortion, but she changes her mind at the last minute and keeps the baby.
- Heterosexual Life-Partners: Halley and Scarlett.
- My Beloved Smother: Halley's mother.
- Prom Baby: Scarlett goes into labor at her school's prom.
- Shut Up, Hannibal!: Halley to her mother, when she gives Halley a speech about how she does not approve of her relationship with Macon or her new friends.
- Someone to Remember Him By: Scarlett has sex with Michael and finds out she's pregnant with his baby after he dies.
- Teen Pregnancy
- Their First Time: A large part of the plot is Halley dithering over whether or not to sleep with Macon. However, Scarlett's pregnancy makes her reluctant to take the risk and when she finally decides to do it, she gets cold feet at the last minute, (not to mention Macon is implied to Really Gets Around) leaving Macon very frustrated, and the ensuing argument in the car about it ends up leaving Halley hospitalised.
- Tomboy and Girly Girl: Scarlett and Halley.