Being a teenager is hard enough without having to deal with your parents' divorce, your sister's wedding, your best friend's pregnancy, and the death of a friend. And falling in love for the first time? That only makes everything harder. At least that's what 17-year-old Halley Martin (Mandy Moore) discovers during her junior year in high school. A confirmed skeptic on love after dealing with her parent's divorce, Halley doesn't understand how her best friend, Scarlett (Alexandra Holden) can suddenly be head over heels for her first serious boyfriend. Or, for that matter, how her older sister, Ashley (Mary Catherine Garrison), can marry stuffy Lewis (Mackenzie Austin) when they seem to disagree all the time. But when her friendship with a quirky schoolmate, Macon Forrester (Trent Ford), ultimately blossoms into romance, Halley suddenly has to reconsider everything she thought to be true about love. Allison Janney stars as Lydia, Halley's mom, a new divorcee dealing with being dumped for a younger woman by her ultra-hip DJ husband, Len (Peter Gallagher).