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Waymon has a great job in real estate and a promising future, but he's also trapped in a loveless longterm relationship. He meets Natalie, a beautiful club-hopping hipster, and quickly falls in love. Realizing he's just not cool enough to attract her on his own, he seeks the help of his friend Bobby, a free-spirited smooth talker who works in the mail room at Waymon's firm and utilizes the predicament as leverage to advance in the company.