Jonathan Tucker as Matthew

Emmanuelle Chriqui as Patty

James DeBello as Rod

Katherine Heigl as Arlene

Larisa Oleynik as Wendy

Jaime Pressly as Cynthia

Marissa Ribisi as Dora

Johnny Green as Crick

Aimee Graham as Ms. Stern

Kristina Anapau as Sasha

Ange Billman as Dana

Rainbeau Mars as Maureen

Mónica Huarte as Janeite #1

Reilly McLaren as Janeite #2

Kristin Herold as Barbara

Anya Marina as Rhonda

Josephine Angelini as Michelle

Julieanne Steger as Penny

Ivana Bozilovic as Rene

Danielle Hoover as Ball Buster

Eric Szmanda as Sam / Computer Nerd

Anita Thomas as Teacher's Pet

Sarah Carmichael as Feminist Wannabe

Crystal Kwon as Man Hater

Nancy Walters as Open Minded Feminist

Bradley K. Ross as Pizza Delivery Guy

Lydia Castro as Hispanic Girl

Alley Mercedes as T-Squared Girl

Lorie Katherine Anderson as High School Girl

Candra Severson as Matthew's Mom

John O'Hara as Matthew - 10 Years Old

Walker Howard as Crick's Partner

Tamara Krinsky as Mystery Girl (voice) / Emily

Farinaz Farrokh as Puppeteer

Allen Payne as Old Guy in Car

Kerstin Lindquist as Sign Language Girl

Ehud Bleiberg as Rene's Father

Madison Brandon as Young Vickie

Terence Michael as Sasha's Boyfriend

Chris Bustard as Penny's Boyfriend

Mike McNet as Cynthia's Boyfriend

Seth Nagel as Michelle's Boyfriend

Esther Gonzalez as Hispanic Mother

Dorlinda Ortiz as Hispanic Kid

Stephanie Ramos as Hispanic Kid

Londonn Corpas as Hispanic Kid

Felicity Mars as Old Lady

Edward Davila as Kung Chang

Laura Gray as Wendy's Mom

Donald Green as Matthew's Dad

Joan Blair as Bathing Suit Woman

Noel Evangelisti as Bathing Suit Woman

Cindy Fried as Bathing Suit Woman

Cynthia Rullo as Bathing Suit Woman

Biljana Filipovic as Girl in Window

Patty Clough as Dorm Room Girl

Sonnie Elahna as Dorm Room Girl

Amy Fioretta as Dorm Room Girl

Holly Houston as Dorm Room Girl

Susan James as Dorm Room Girl

Anna Khomute as Dorm Room Girl

Lon Pho as Dorm Room Girl

Kimberly Reeves as Dorm Room Girl

Adrienne Rey as Dorm Room Girl

Tanya Tyranny as Dorm Room Girl

Maria Strain as Dorm Room Girl

Tanisha Grant as Sorority Girl (uncredited)

Gina Hiraizumi as Baby Carriage Girl (uncredited)

Agnieszka Musiala as Tall Girl (uncredited)

Christopher Mulai as