Jesse Metcalfe as John Tucker

Brittany Snow as Kate

Ashanti as Heather

Sophia Bush as Beth

Arielle Kebbel as Carrie

Penn Badgley as Scott

Jenny McCarthy-Wahlberg as Lori

Terrell J. Ramsey as Tommy

Kevin McNulty as Basketball Coach

Patricia Drake as Coach Williams

Amanda Li as Spelling Bee Girl

Jeffrey Ballard as Cute Boy

Taylor Kitsch as Justin

Steve Bacic as Skip #1

Dean Wray as Skip #2

Johnny Cuthbert as Skip #3

Aaron Dudley as Skip #4

Marc Menard as Skip #5

Dan Payne as Skip #6

Mercedes de la Zerda as Stoner Girl

Brendan Penny as Teammate #1

Taurean Mills as Teammate #2

Nicole LaPlaca as Molly

Chelan Simmons as Crying Waitress

Nancy J. Lilley as Coach Claypoole

Yalda Etessam as Goth Girl

Devon Weigel as Volleyball Girl

Alf Humphreys as Detention Teacher

Woody Jeffreys as Helmut (Beth's Photographer)

Samantha McLeod as Holly (John's Movie Date)

Diana Ha as Chinese Woman In Theatre

Donald Fong as Chinese Man In Theatre

Karlie Locke as Sign Language Girl

Stephanie A. Locke as Sign Language Girl

Fulvio Cecere as Chemistry Teacher

Lucas McCann as Game 2 Opponent

Bruce Morrison as Referee #2

Barbara Kottmeier as Beautiful Girl #1

Nicki Clyne as Beautiful Girl #2

Katya Virshilas as Beautiful Girl #3

Nicole Fraissinet as Nancy

Stuart Cowan as Freshman Flower Boy

Julie Patzwald as Becky From Student Council

Connor Widdows as Freshman At Beach

Kristian Blight as Bass - 'People In Planes'

Gareth Jones as Lead Vocals - 'People In Planes'

John Maloney as Drums - 'People In Planes'

Peter Roberts as Guitar - 'People In Planes'

Ian Russell as Keyboards - 'People In Planes'

Amanda Crew as Hallway Girl

Emily Tennant as Hallway Girl

Victor Z. Isaac as Guy At Party #1

Braden Williams as Guy At Party #2

Kyle C. Coleman as Guy At Party #3

Greg Cipes as Guy At Party #4

Amber Borycki as Jennifer

Meghan Ory as Jill

Alan Shearman as Teacher In Thong #1

Archie Hahn as Teacher In Thong #2

Chelsea Florko as Freshman Girl (uncredited)

Angela Marie Fong as Cheerleader (uncredited)

Jessica Harmon as Girl at Party (uncredited)

Almeera Jiwa as Freshman Girl #1 (uncredited)

Maggie Ma as Freshman Girl #2 (uncredited)

Heather McEwen as Freshman Girl #3 (uncredited)

Steffinnie Phrommany as Student (uncredited)

Christina Schell as Dancer (uncredited)

Stephane Savoie as Alex (uncredited)