When a man decides to ask his girlfriend to marry him, he attends a family gathering at their seaside estate.
Wade Walker is eager to propose to his girlfriend, Grace Peeples. But after a year of living together, the beautiful, successful Grace is still cagey about introducing average guy Wade to her ambitious, upper crust family. So when Grace leaves for an annual reunion at her parents' swanky Sag Harbor compound, Wade decides to crash the gathering, charm his soon-to-be in-laws and slip a ring on Grace's finger. However Wade's plans go hilariously awry when he meets the high-powered, seemingly picture-perfect family who'll do whatever it takes to keep up appearances. Wade soon finds himself caught in a web of white lies and comic dysfunction, and realizes that his only hope of ever marrying Grace means a take-no-prisoners face-off with Judge Peeples, Grace's disapproving dad who won't accept anything less than the very best for his favorite daughter.