Waymon features a excellent job in realestate and also a promising future, but he has also trapped in a relationship. He immediately falls in love, and meets with a beautiful club hopping hipster, Natalie. Knowing he's simply not cool enough to attract her on his own, he seeks the help of his friend Bobby, a free-spirited smooth talker who utilizes the predicament as leverage to advance in the company and works in the mail room in the firm of Waymon.