"Failure to Launch" stars Matthew McConaughey as a 35-year-old man named Tripp who is still living at home with his parents, Al and Sue, played by Terry Bradshaw and Kathy Bates. When Al and Sue's friends reveal how they hired an expert to rid them of their own grown son who was still living at home, the couple decide to hire her as well to convince Tripp to leave the nest.
Sarah Jessica Parker plays Paula, a woman whose business specializes in grown men who have failed to move out on their own. She believes this "failure to launch" is due to low self esteem, which she seeks to correct by pretending to date these men. The men then transfer their attachment of their parents to Paula and eventually move out on their own.
Paula meets her match in Tripp, who does not have the typical self-esteem issues of her usual clients. Paula avoids being dumped by Tripp by sleeping with him, which initiates a real relationship between the two. Tripp's good friend, Ace, finds out Paula was hired by Tripp's parents and blackmails her in order to get Paula to set up a date between him and Paula's roommate, Kit. The pairing results in a successful relationship, but Ace lets Paula's secret slip to another friend, Demo, who in turn tells Tripp.
Upon finding out Paula was hired by his parents to make him move out, Tripp breaks up with Paula. It then falls upon Tripp's parents and friends to help the two reconcile.