Maddy is 32 years old, she has lived all her life in Montauk, a resort town near New York. The rich are buying up real estate here, taxes are constantly rising, and the girl is trying to keep the house she inherited from her mother, so she finds herself up to her ears in debt. Having lost her car and the opportunity to taxi, in exchange for a car, she decides to help rich parents who are worried that their 19-year-old son will soon go to college, but he still won't get out of his shell. Maddy's task is to take the guy's virginity, but it turns out to be not so easy to do.