Halley Marie Martin (Mandy Moore) is a 17-year-old high school student who is disillusioned with love after seeing many dysfunctional relationships around her. Her parents are now divorced and her father, Len Martin (Peter Gallagher), a radio talk show host, has a new young girlfriend that the entire family despises. Her mother, Lydia (Allison Janney), is now always alone while her sister, Ashley, is so overwhelmed by her upcoming wedding with Lewis Warsher that she barely exists in the house. The shallowness of all the teens at her school convinces Halley that finding true love is impossible.
When Halley walks in on her best friend Scarlett having sex with her boyfriend, the high school soccer champ, Michael Sherwood, Halley tries to warn her of the complications that lie ahead. Ignoring her advice, Scarlett embarks on a summer fling with Michael. In the meantime, Halley must deal with Ashley and the rest of the Martins must deal with her soon-to-be in-laws, Lewis' overbearing Southern parents, who have an African American maid. In the meantime, Halley runs into classmate Macon Forrester, a slacker who never shows up for biology and is more interested in having fun than school work. He is Michael Sherwood's best friend.
Then a few weeks later, Michael dies of a heart defect on the soccer field while Halley, Scarlett and other classmates watch helplessly. This event changes the lives of Halley and Scarlett forever. While Scarlett does her best to look beautiful for Michael at his funeral, Macon gives a moving speech about his friend. Struggling with Michael's death, Scarlett, at age sixteen, soon learns that she is pregnant with his child. With Halley at her side, Scarlett reveals the pregnancy to her mother.
Halley's father, Len Martin, marries his mistress, Lorna, in a beach-side ceremony, with guests from all over the world, or "within his radio frequency", as Halley puts it.
Halley and Macon eventually start a relationship. He takes her to his and Michael's favorite hangout and once come close to having sex. Halley and her mother get into an argument and on New Year's Eve, Halley sneaks out with Macon to a party. Again, they come very close to having sex but this time Halley stops it and Macon is upset. On their way home, they are both upset and distracted and hit a tree. Halley gets a broken arm, but otherwise they both walk away from it unharmed, but Halley breaks up with Macon saying that she can't wait around for him to grow up. Later things go awry when Halley finds Ashley drunk on the family's front porch. Finding a male stripper's thong around her neck, Halley witnesses the break-up of her sister's engagement. She also learns that her mother sneaks out once a week to have sex with a man she met a couple of weeks previously, Steve. After another make-up, Lewis proposes to Ashley again, this time at a crowded airport: she says yes.
On the day of Ashley and Lewis' wedding, Macon bursts into Len's radio studio, professing his apologies and love to Halley. He then heads to the wedding. On the way, he finds Scarlett, who insisted on walking to the wedding, going into labor on the side of the road. He puts her in the car and walks into the wedding, getting Halley's attention. The three rush to the hospital, leaving Scarlett's mother behind in the rush.
While Scarlett is having her baby, Halley makes a list of all the little things she hates about Macon, the way his hair falls over his face, the way his voice gets low when he's serious, the way he bites his lip when he's nervous and the way his eyebrow twitches. Halley playfully uses Macon's 'Jedi Mind Trick' and they kiss and dance briefly in the hallway. The movie ends as Halley and Macon embrace and viewers see that Scarlett gave birth to a baby boy.Mandy Moore – Halley Marie Martin
Allison Janney – Lydia Williams Martin
Trent Ford – Macon Forrester
Alexandra Holden – Scarlett Smith
Dylan Baker – Steve Beckwith
Nina Foch – Grandma Halley Williams
Peter Gallagher – Len Martin
Mackenzie Astin – Lewis Gibson Warsher II
Connie Ray – Marion Smith
Mary Garrison – Ashley Renee Martin
Sonja Smits – Carol Warsher
Laura Catalano – Lorna Queen
Ray Kahnert – Donald Sherwood
Andrew Gillies – Buck Warsher
John White – Michael Sherwood
Alison MacLeod – Sharon Sherwood
Bill Lake – Ed
Charlotte Sullivan – Elizabeth Gunderson
Philip Akin – Mr. Bowden
Claire Crawford – Seamstress
Ennis Esmer – Ronnie
Thomas Hauff – Minister
- Billy S. - Skye Sweetnam
- Do You Realize?? - The Flaming Lips
- It's on the Rocks - The Donnas
- Why Can't I? - Liz Phair
- Wild World - Beth Orton
- Not Myself - John Mayer
- That's When I Love You - Aslyn
- Thinking About Tomorrow - Beth Orton
- Promise Ring - Tremolo
- Take The Long Road And Walk It - The Music
- Waves - Marjorie Fair
- Surrender - Echo
- Wild World - Cat Stevens
The film's reviews were generally negative, with a score of 28% in review aggregator Rotten Tomatoes based on 93 reviews.
In its opening weekend, the film grossed $5,809,960 million in 2,319 theaters in the United States and Canada, ranking #8 at the box office. By the end of its run, How to Deal grossed $14,195,227 domestically and $112,905 internationally, totaling $14,308,132 worldwide.