When Steve Healy, a lousy employee at the substandard company Pineapple Insurance unknowingly irritates an Insurance company Auditor, his Uncle's company is in danger of being shut down permanently after 30 years of operation. After assigning her daughter to give a thorough audit of the company, a spiteful Director at the Department of insurance (Donna Murphy) is encouraged that her daughter Celeste will get the job done. What she did not count on is that her socially awkward daughter may be falling in love with a top notch loser.