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

Andy O'Connor

Groom at Lake

Amanda Dane

Bride at Lake

Valerie Laury

Minister

Rachel Wirtz

Cinderella

Keaton Simons

Guitar Player

Billy Concha

Pedi Cab Guy

Paul Melendy

Randall

Jonathan De Azevedo

Juan

Ava Gaudet

Jody

Libby Collins

Centerpiece Arranger

Dennis Dugan

Eddie Stone

Alex Mack

Champagne Girl

Mark Lainer

Nick Matthews

Cailey Calisi

Marcee

Natalia Grace

Foreign Female Contestant

Abbey Dubin

Sharon

Gabriel Pimentel

Verne

Becky Bass

Gianna

Levon Panek

Donald

Nick Slade

Habib 1

Tarek Moussa

Habib 2

Pesach Walter

David

Benz Veal

Michael (Smug Contestant)

Gail Bennington

Tina

Sally Meehan

Meg

Courtland Jones

Waitress

Jen Mauceri

Duckboat Lady Tourist

Victor Antolini

Victor

Gary Cormier

Gary

Adam Mastroianni

Baseball Cap Guy

Maximo Duran

Crash Couples Cameraman

Kiara Pichardo

Girl in Bathroom

Jaison Hunter

Bert

David Bernon

Yankee Fan

Vicky Nikollo-McCarthy

Yankee Fan's Wife

Brandon Scales

Gail's Cameraman

Michael Collins

Dr. Offerman

William Xifaras

Menny

Kevin Wiles Jr.

Ivan

Ellen Collins

One of Ritchie's Ladies

Oscar Foster

Carriage Driver

Alexandra Pierre-Etienne

Female Sax Player

Jeff Masin

One Man Band

Rob Norton

Perry Blake

Whitney Meyer

Zhopa's Dance Partner

Hannah Jane Doyon

Bridesmaid (uncredited)

Kimberly Howe

Bridesmaid (uncredited)

Ineke Garbacz

Red Sox Fan (uncredited)

Heidi Garrow

Dancer (uncredited)

Janelle Feigley

Dancer / Wedding Guest (uncredited)

Joseph Oliveira

Wedding Guest (uncredited)

Nadezhda Russo

Woman for Ritchie (uncredited)

Forest Quaglia

Pedestrian (uncredited)

Ben Bunnag

Sushi Chef

Christopher Mendez

Svetlana's Lap Dance Patron (uncredited)