Adrian Grenier

Sean McAllister

Selma Blair

Glenn McAllister

Bailey Chase

Rick McAllister

Melora Walters

Evie Flores

Drea de Matteo

Ana

Mary Lynn Rajskub

Kim Wells

Tim DeKay

Sex Ed Video Teacher

Daniel Hugh Kelly

Dick McAllister

Joshua Rush

Eli McAllister

Hudson Thames

Teenage Sean

Cheyanne Cope

Teenage Glen

Justin Prentice

Teenage Rick

Marco James

Teenage John

Drew Powell

Tim Hollister

Eddie Matos

John Garcia

Wayne Wilderson

Ben Kingston

Lyle Kanouse

Hal Spencer

Ian Duncan

Devon North

Richard Riehle

Father Joe

Erica Gimpel

Shanti

Googy Gress

Dan Cornfelder

Joanna Ranee Wood

Woman in Suit

Betsy Cramer

Woman in Trench Coat

Adam Hochstetter

Snotty #1

Carsen Warner

Snotty #2

Sean Ryan Fox

Wolf Hollister

Holly Houk

Ella

Joe Massingill

Teenage Tim

Serena Bateman

Teenage Tim's Girlfriend

Max Ermakov

Jock #1

Sean Bremner

Jock #2

Yetta Gottesman

Chay Caldwell Lara

Elena Aaron

Nan Allarid

Justin Lopez

Teacher/Coach

Riley Lennon Nice

Tyler

Elizabeth Tripp

Monica

Karyn Quackenbush

Miss Goddard

Jeffrey De Serrano

Coach Frank

Rebecca Benzell

Teenage Kim

Rosie Trujillo

Teenage Mercedes

Wajid

Sai Baba

Jody Hart

Charlie Cornfelder

Brian J. Carter

Bowling Manager

Jennifer Carta

Sherry

Valorie Hubbard

Hal's Wife

Dylan Nalbandian

Young Sean

Weston McClelland

Young Rick

Jennifer Ashley Greene

Mercedes

Andy McDermott

Skydiving Instructor