Halley Martin (MANDY MOORE) is a 17-year-old junior in high school who's disillusioned about love and relationships. That isn't exactly surprising considering that her flamboyant deejay dad, Len (PETER GALLAGHER), has just divorced her bitter mom, Lydia (ALLISON JANNEY), so that he can elope with his on-air co-host.
She also sees that her older, high maintenance sister, Ashley (MARY CATHERINE GARRISON), is always fighting with her fiancé, Lewis (MACKENZIE ASTIN), and simply can't understand why people feel the need to get together when it appears they'll inevitably break up. It doesn't help that Halley's best friend, Scarlett (ALEXANDRA HOLDEN), has fallen for a guy and is oblivious, at least in Halley's eyes, of the romantic icebergs that loom ahead.
Despite all of that, Halley finds herself attracted to her rebellious and unconventional classmate Macon Forrester (TRENT FORD). Yet, despite his desires, she doesn't want to fall for him. As the year quickly zips along, and as Ashley and Lewis' wedding date approaches, and tragedy and surprise visit her friend, Halley tries to sort out her feelings about the various familial and romantic relationships in her life.