Montauk, New York. With her childhood home drowning in long-overdue property taxes, carless Uber driver Maddie needs a money-making plan to stay afloat. And then, desperate Maddie chances upon a proper lifesaver: an unusual Craigslist ad, where a concerned couple seeks a young woman to date their socially awkward 19-year-old son before he goes to Princeton. That should do the trick. But everyone knows there's no such thing as a foolproof plan. How hard can it be to bring a quiet, inexperienced introvert out of his shell?—Nick Riganas