Matt LeBlanc as Charlie Darby

Ali Larter as Molly Kingston

Adam Rodriguez as Jason Kerwick

Ashley Williams as Felicia

Rebecca Naomi Jones as Nancy Kerwick

Carsen Warner as Timmy Clark

Connie Sawyer as Bebe

Cameron Richardson as Michelle

Richard Riehle as Father

Jennifer Rhodes as Mother

Rachael Harris as Roberta

Kristen Johnston as Katherine

Chevy Chase as Lester Horn

Ida Anderson as Cashier

Bella Spencer as Becky

Tamer Aziz as Waiter

Walter Black as EIghties Guy

Santiago Gudino as Matt

Raymond Ochoa as Shane

Carmina Garay as Sharon

Madison Wenn as Amy

Brian Drolet as Josh

Juette Raphael as Lifeguard

Soraya Andrade as Hannah

Elizabeth Ho as Tanya

Louise Griffiths as Jacinda

Vincent Giovanni as Antonio

Laura James as Italian Woman

Jason Scott Jenkins as Concierge

Kate Miller as Ballet Teacher

Andrew Scully as Waiter (uncredited)

Allison Gold as School Student (uncredited)