Maddy, 32 years old, has spent her whole life in Montauk, a resort town near New York. The rich are buying up property here, taxes keep rising, and the girl is trying to hold onto the house she inherited from her mother, so she ends up up to her ears in debt. Having lost her car and the ability to taxi, she agrees to help her wealthy parents in exchange for a car. They worry that their 19-year-old son will soon start college, and he just can't seem to get out of his shell. Maddy's task is to deflower the guy, but it turns out not to be that easy.