Driving Me Crazy (2012)

Meet Elliot Brown. He is one of Brooklyn's most neurotically sweet and eligible bachelors . . . who also happens to be pushing forty and living with his mother. Not getting any younger, Elliot embarks on a 3000 mile road trip across the country to take a chance on a girl he has never met. His travel companion? Her fun-loving sister. Now, he must face his fears, confront his past and learn to take risks to be the man worthy of her love. Buckle up. It's going to be a crazy drive.