I'll Take You There (1999)

Bill/Reg Rogers still hasn't gotten over his wife leaving him 3 months ago and moving in with his (ex-) best friend. He gets forced on leave at work for being unproductive. His sister tries to help him and arranges a date with Bernice/Ally Sheedy which goes awfully wrong. Without consent, she crashes at his place and demands an apology. She lets him borrow her car to drive to his wife and talk to her but hides in the car. It becomes a road trip with a stop at Bernice's dying grandma. Bill and Bernice get to know each other.