Ryan is a middle manager at the city’s fourth largest insurance firm. He’s also in love with with the ‘new girl’, his co-worker, Amy. Trouble is, she doesn’t know he exists, because he’s way too shy to talk to her. Amy sits near the office watercooler, so Ryan spends his whole day drinking gallons of water just for an excuse to be near her. Never quite working up the bravery to tell her how he feels, he just keeps putting away the H2O. Finally, Ryan’s buddy Jack, and Amy’s next door cube-neighbor, steps in and presents Ryan with an ultimatum: go big, or go home. And on this particular day, Ryan will finally see his chance to tell her how he feels… in the most unlikely of places.