Wade Walker has been dating Grace Peeples for a year and he's desperate to meet the rest of the family, if only to ask her father for her hand in marriage. However, she still has major reservations about it given that her father is a formidable federal judge. When she jets off to the east coast for her annual family reunion in the Hamptons, Wade bravely follows determined to show his future father-in-law that he is good enough to join them as his daughter's future husband. Things don't go according to plan with an immediate personality clash and several major gaffes on the part of Wade, but he soon learns over the course of a very eventful weekend that there's more to this seemingly perfect family than meets the eye and he's prepared to stand up to them no matter what the consequences.
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Jason and Cynthia (Bateman and Bell) are a workaholic couple approaching their marriage as a business, so they propose to their friends a couple-building holiday in a tropical paradise. Dave and Ronnie (Vaughn and Akerman) need a break form their busy lives, Joey and Lucy (Favreau and Davis) hope to spend as much time holidaying apart as possible, and Shane (Love) brings along his new, young girlfriend (Walsh). Despite the spectacular location, it's not remotely what any of them expect, especially when love guru Marcel (Reno) starts his workshops.
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