The movie: Failure to Launch (2006)
The player(s): Matthew McConaughey, Terry Bradshaw, Kathy Bates and Sarah Jessica Parker

In this poorly received rom-com, Tripp (McConaughey) is an otherwise well-adjusted 35-year-old who falls prey to one frequent man child tendency: an unwillingness to leave the comforts of his childhood home (yes, mom and dad still live there, too). Until his parents—anxious for their nest to be emptied—hire an "expert" dater (Parker) tasked with building up Tripp's self-esteem and desire to have a place of his own in the process.