Carolina Mirabeau (Julia Stiles) was raised 'free-spirited' with two sisters by eccentric, domineering grandma Millicent in the country. Carolina's city neighbor, talented and witty Jewish author Albert Morris (Alessandro Nivola), is her best friend, confident and the wacky family's favorite guest. Yet she begins dating Heath Pierson (Edward Atterton), an 'all too perfect' upper class brilliant Britton, whom she met in the TV studio where she's fired as dating show candidates-screener. But the past and some truths catch up with all of them.
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