Tripp(Matthew McConaughey) is a whimsical 35 year-old man going through relationship troubles. His troubles seem to begin and end with the fact he lives with his parents. His parents, Al and Sue(Terry Bradshaw and Kathy Bates) have just been told by their friends that Tripp needs to meet the right girl, if they ever want their son to leave. Fortunately for Al and Sue Tripp meets Paula(Sarah Jessica Parker) who has an amazing personality to overcome her equine features and blatant violations push-up bra safety.Unbeknownst to Tripp, Paula has been hired by his parents to become his inspiration to move out. Sue also helps spur Tripp out of the house by telling him to do more chores. We then learn that Tripp is a boat salesman and he is lying to Paula in an attempt to have intercourse with her. Paula is not annoyed by this fact and continues to play him. Tripp confides to his friends that he really likes Paula and they inform him that he is doomed to fail because of his living situation.Tripps second date with Paula is another whacky disaster as his injured hand leads him to fumble with sushi. Paula then calls Tripp to the vets office to help her with the staged euthanasia of her dog. Tripp then takes Paula to play paintball, and Ace(Justin Bartha) meets Kit(Zooey Deschanel). It turns out Kit is also in on the deceit to lure Tripp out of the house. Paula believes that her job is almost done and that Tripp has fallen for her.While Tripp is with his friends surfing he tells them that he has to get rid if Paula because she is too serious. So Tripp takes her home where his parents lie to him about knowing Paula. Tripp is suspicious that Paula is not annoyed by his living situation. Sue tells Paula that Tripp brought her to the house to break up with her. Paula then turns up her prostitution up a notch, and sleeps with him in return for payment by his parents.Ace then catches Paula with another client and Paula then barters Kit to Ace in return for his silence. Kit then falls for Ace as he offers a means to kill a federally protected bird. Meanwhile, during a date with Tripp, Demo(Bradley Cooper) tells Paula that he knows what she is doing and tell her more about Tripp and why he hasnt left home. Demo then tells Tripp what he told Paula and that she is being paid by his parents.Tripp then makes a meal for Paula and his parents and tells them he wants Paula to move in with him, but then unexpectedly turns the tables and tell them he knows Paula is a prostitute, and leaves. Suddenly Tripp and Paula both realize, thru help of their friends, that they are unhappy.Sue gets the gang together and they concoct a plan to get Tripp and Paula back together. Tripp is then beaten and tied up and falsely imprisoned in a bugged house with Paula. They have a talk and get back together while they make love on a web cast that their friends are watching. They then sail off into the sunset, and more whacky adventures.