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.

• Island World
• Joseph C. Phillips
• Halle Berry
• Tommy Davidson
• Anne-Marie Johnson
• Samuel L. Jackson
• Kim Coles
• Sam Rockwell
• Denis Leary