Diane Keaton as Sara

Jeremy Irons as Lawrence Philips

Maggie Grace as Jessie

Diego Boneta as Mack

Andrew Bachelor as Captain Ritchie

Veronica Ferres as Bev

Jesse McCartney as Lenny

Melinda Hill as Svetlana / Olga

Elle King as Jordan

Chandra West as Gail Lovejoy

Caroline Portu as Liz Rafferty

Todd Stashwick as Zhopa

Andy Goldenberg as Jimmy Barton

Richard Kline as Steve

Dennis Staroselsky as Robert Barton

JinJoo Lee as Yoni

Dustin Tucker as Pilot

Andy O'Connor as Groom at Lake

Amanda Dane as Bride at Lake

Valerie Laury as Minister

Rachel Wirtz as Cinderella

Keaton Simons as Guitar Player

Billy Concha as Pedi Cab Guy

Paul Melendy as Randall

Jonathan De Azevedo as Juan

Ava Gaudet as Jody

Libby Collins as Centerpiece Arranger

Dennis Dugan as Eddie Stone

Alex Mack as Champagne Girl

Mark Lainer as Nick Matthews

Cailey Calisi as Marcee

Natalia Grace as Foreign Female Contestant

Abbey Dubin as Sharon

Gabriel Pimentel as Verne

Becky Bass as Gianna

Levon Panek as Donald

Nick Slade as Habib 1

Tarek Moussa as Habib 2

Pesach Walter as David

Benz Veal as Michael (Smug Contestant)

Gail Bennington as Tina

Sally Meehan as Meg

Courtland Jones as Waitress

Jen Mauceri as Duckboat Lady Tourist

Victor Antolini as Victor

Gary Cormier as Gary

Adam Mastroianni as Baseball Cap Guy

Maximo Duran as Crash Couples Cameraman

Kiara Pichardo as Girl in Bathroom

Jaison Hunter as Bert

David Bernon as Yankee Fan

Vicky Nikollo-McCarthy as Yankee Fan's Wife

Brandon Scales as Gail's Cameraman

Michael Collins as Dr. Offerman

William Xifaras as Menny

Kevin Wiles Jr. as Ivan

Ellen Collins as One of Ritchie's Ladies

Oscar Foster as Carriage Driver

Alexandra Pierre-Eitenne as Female Sax Player

Jeff Masin as One Man Band

Rob Norton as Perry Blake

Whitney Meyer as Zhopa's Dance Partner

Hannah Jane Doyon as Bridesmaid (uncredited)

Kimberly Howe as Bridesmaid (uncredited)

Ineke Garbacz as Red Sox Fan (uncredited)

Heidi Garrow as Dancer (uncredited)

Janelle Feigley as Dancer / Wedding Guest (uncredited)

Joseph Oliveira as Wedding Guest (uncredited)

Nadezhda Russo as Woman for Ritchie (uncredited)

Forest Quaglia as Pedestrian (uncredited)

Cassidy Neal as (uncredited)