How to Deal (2003)

Synopsis
Teen pop star Mandy Moore stars in the romantic comedy How to Deal. Directed by British filmmaker Clare Kilner, the script is based on two of author Sarah Dessen's popular teen novels: Someone Like You and That Summer. Halley (Moore) is a teenager trying to make sense of the faltering romantic relationships within her immediate social sphere. Her mother, Lydia (Allison Janney), can't seem get a date, while her father (Peter Gallagher) is getting remarried to a woman that nobody seems to like. Halley's wedding-obsessed sister, Ashley (Mary Catherine Garrison), is engaged to Lewis (MacKenzie Astin), a guy that is completely wrong for her. Meanwhile, bad boy Macon Forrester (Trent Ford) won't leave Halley alone. Just when she decides to become cynical about love because of all the romantic disappointments around her, a troubled situation involving her best friend Scarlett (Alexandra Holden) changes her outlook. ~ Andrea LeVasseur, All Movie Guide