You're So Cupid

Lauren Holly

Audrey Valentine

Brian Krause

Daniel Valentine

Jeremy Sumpter

Connor

Caitlin E.J. Meyer

Lily Valentine

Danielle Chuchran

Emma Valentine

Amanda Gallo

Ashley

Melise

Megan

Chad Hively

Elliot

Jessica Jackson

Piper

Susan Phelan

Mrs. Porter

Zack Phifer

Principal Barlow

Logan Rogan

Marvin

Nikola Clark

Rita

Dayne Rockwood

Tyler

Michael James Brown

Pizza Delivery Guy

Juliette Lyde

Young Emma Valentine

Grace Hallows

Young Lily Valentine

Lindsay Bird

Young Audrey

Aaliyah Lightfoot

Cute Girl

Luke Porter

Wentworth

Ethan Lyde

Kissing Boy

Monique Baird

Kissing Girl

Adam Baird

Pretentious Thug

Zack Bullock

Handsome Thug

Adam Kaiser

Really Cute Boy

Shalaina Castle

Candice

Bryton Catlett

Student (uncredited)

Christopher K. Hagadone

Kickball Player (uncredited)

Crystal Sargent

Student (uncredited)

Stacey Ann Turner

Student (uncredited)

Lauren Wright

Student (uncredited)