How Do You Know

Reese Witherspoon

Lisa

Paul Rudd

George

Owen Wilson

Matty

Jack Nicholson

Charles

Kathryn Hahn

Annie

Mark Linn-Baker

Ron

Lenny Venito

Al

Molly Price

Coach Sally

Ron McLarty

George's Lawyer

Shelley Conn

Terry

Domenick Lombardozzi

Bullpen Pitcher

John Tormey

Doorman

Teyonah Parris

Riva

Tony Shalhoub

Psychiatrist

Dean Norris

Softball Coach

Donna Dundon

Annie's Mom