Plot

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.—Darin Munnell

Meet Steve Healy, sales associate at Pineapple Insurance. Steve is a man that is currently "failing uphill." No matter what he does wrong, he will most likely still have a job (his Uncle George owns the company), live in a moderately comfortable apartment, and coast through his life; if his drinking problem doesn't kill him first. Steve also works with his best friend, Lawrence and the super sexy 24/7 party girl, Lucy. It may not be the American Dream, but Steve is relatively content hanging near the bottom of the barrel... Until Celeste Murphy walks into the office.

Celeste is the daughter of Donna, who is in charge of the Los Angeles Department of Insurance. The DOI is a consumer watchdog group that is essentially a pain in the ass for all Auto Insurance companies in the city. Celeste walks in during one of Steve's morning hangovers to inquire about having her insurance premium lowered. After some crude flirtations, Celeste leaves and reports her less than stellar experience to her mother. After very little internal debate, Donna decides she is more than happy to audit Pineapple Insurance.

At this moment, our gang is going to have to change everything! No more harsh language in the workplace, no more internet surfing for NSFW videos, no more drinking on the clock, and worst of all... no more rude behavior toward customers! Change is never easy. One wrong step, Pineapple Insurance will be boarded up and condemned for all times. Sadly, making their business over is unlikely a successful plan they will be able to execute, until an unexpected life preserver is tossed their way... Celeste may be attracted to Steve!

This attraction is a little unusual. Steve is book smart, but a loser. Celeste is great at her job, but has a pitiful social life. On the bright side, maybe they can make up for each other's shortcomings if they started dating. On the negative side, Donna has a major influence on her daughter's life and she despises Steve and his Uncle George.