
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.

as Waymon

as Natalie

as Bobby

as Diedre

as Monroe

as Millicent

as Gary

as Jake

as David

as Drake

as Roland Halloran

as Darryl

as Hustler

as Olivia

as Married Man

as Cocktail Waitress

as Sheila

as Leroy Halloran

as Mr. Atwell

as Band at Lola's

as Donna