Maggie Grace as Jessie

Diane Keaton as Sara

Jeremy Irons as Lawrence Philips

Diego Boneta as Mack

Todd Stashwick as Zhopa

Jesse McCartney as Lenny

Andrew Bachelor as Captain Ritchie

Dennis Dugan as Eddie Stone

Chandra West as Gail Lovejoy

Veronica Ferres as Bev

Richard Kline as Steve

Kimberly Howe as Bridesmaid

Elle King as Jordan

Kiara Pichardo as Girl in Bathroom

Melinda Hill as Svetlana / Olga

Ava Gaudet as Jody

Caroline Portu as Liz Rafferty

Nadezhda Russo as Woman for Ritchie

Heidi Garrow as Dancer

William Xifaras as Menny

David Bernon as

Dustin Tucker as Pilot

Whitney Meyer as

Andy Goldenberg as Jimmy Barton

Dennis Staroselsky as Robert Barton

Ellen Collins as Ella (Ritchie's Fan)

Rob Norton as Perry Blake

Billy Concha as Pedicab Guy

Brandon Scales as Gail's Cameraman

Keaton Simons as Guitar Player

Joseph Oliveira as Wedding Guest

Ineke Garbacz as Red Sox Fan

Cassidy Neal as

JinJoo Lee as

Sally Meehan as Meg

Forest Quaglia as Pedestrian

Janelle Feigley as Dancer - Wedding Guest

Hannah Jane Doyon as Bridesmaid