Diane Keaton

Sara

Jeremy Irons

Lawrence Philips

Maggie Grace

Jessie

Diego Boneta

Mack

Andrew Bachelor

Captain Ritchie

Veronica Ferres

Bev

Jesse McCartney

Lenny

Melinda Hill

Svetlana / Olga

Elle King

Jordan

Chandra West

Gail Lovejoy

Caroline Portu

Liz Rafferty

Todd Stashwick

Zhopa

Andy Goldenberg

Jimmy Barton

Richard Kline

Steve

Dennis Staroselsky

Robert Barton

JinJoo Lee

Yoni

Dustin Tucker

Pilot

Billy Concha

Pedi Cab Guy

Paul Melendy

Randall

Ava Gaudet

Jody

Dennis Dugan

Eddie Stone

Mark Lainer

Nick Matthews

Gabriel Pimentel

Verne

Benz Veal

Michael (Smug Contestant)

Courtland Jones

Waitress

Kiara Pichardo

Girl in Bathroom

Jaison Hunter

Bert

David Bernon

Yankee Fan

Brandon Scales

Gail's Cameraman

William Xifaras

Menny

Rob Norton

Perry Blake

Whitney Meyer

Zhopa's Dance Partner

Ineke Garbacz

Red Sox Fan (uncredited)

Janelle Feigley

Dancer / Wedding Guest (uncredited)

Forest Quaglia

Pedestrian (uncredited)