Lindsay Lohan as Ashley Albright

Chris Pine as Jake Hardin

Samaire Armstrong as Maggie

Bree Turner as Dana

Faizon Love as Damon Phillips

Missi Pyle as Peggy Braden

Makenzie Vega as Katy

Carlos Ponce as Antonio

Danny Jones as Danny Jones

Tom Fletcher as Tom Fletcher

Harry Judd as Harry Judd

Dougie Poynter as Dougie Poynter

Tovah Feldshuh as Madame Z

Dane Rhodes as Mac

Jaqueline Fleming as Tiffany

Chris Carmack as David Pennington

Ira Hawkins as Doorman Oscar

J.C. Sealy as Aunt Martha

Mikki Val as Tough Jailbird

Marcus Hester as Tom Gilpin

Ameer Baraka as Phillips Minion

Anne Ewen as Phillips Minion

Thomas Tah Hyde III as Phillips Minion

Mark Wystrach as Phillips Minion

Strawn Bovee as Mrs. Pennington

Gerry Vichi as Diner Owner

Dennis Wit as Diner Bacon Guy

Kenny Alfonso as Party Detective

Ray Garvey as Party Cop

Larry Gamell Jr. as Jail Deputy (as Lawrence C. Gamell Jr.)

Rome Kanda as Zuki - Japanese Maitre D'

Jon Manfrellotti as Palace Cab Driver

Deanna Miller as Palace Model

Erik Liberman as Palace Clipboard Man

Al Roffe as Lottery Cashier

Dean Cochran as Kissing Groom

Mary Firestone as Bride

Matthew Morgan as Kissing Street Performer

Dariush Vollenweider as Kissing Hospital Patient

Denis Gawley as Steam Room Guy

Russ Klein as Steam Room Guy

Loring Murtha as Kissing Jogger

Kevin Scanlon as Haz-Mat Officer

David Jensen as Stage Manager (as David E. Jensen)

J.P. Patterson as Recording Engineer

Kathy Tong as Art Gallery PR Woman

Frank Ferrara Sr. as Central Park Cop

Kasie Head as Central Park Jogger

Hannah Tointon as Concert Goer

Kayla Ewell as Janet the Bank Teller

Craig 'Radio Man' Castaldo as Bicycle Driver (uncredited)

John Bernard Martin as Bernie - Jake's Driver

Alexandra Apjarova as Sky Dancer

Christine Van Loo as Sky Dancer

Jennifer Arden as Party Dancer

Tiffany Jackson as Party Dancer (as Tiffany J. Billiot)

Michelle N. Gibson as Party Dancer

Kerry Lambert as Party Dancer

Luke Sexton as Party Dancer

Misty Marshall as Mud Dancer