
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.
Genres:

Joseph C. Phillips as Waymon

Halle Berry as Natalie

Tommy Davidson as Bobby

Anne-Marie Johnson as Diedre

Samuel L. Jackson as Monroe

Kim Coles as Millicent

Sam Rockwell as Gary

Denis Leary as Jake

David Marshall Grant as David

Jon Cypher as Drake

James McDaniel as Roland Halloran

Joe Torry as Darryl

Isaiah Washington as Hustler

Novella Nelson as Olivia

Kevin Hooks as Married Man

Ellen Cleghorne as Cocktail Waitress

Annie Golden as Sheila

Paul Butler as Leroy Halloran

Ira Wheeler as Mr. Atwell

Jodeci as Band at Lola's

Susan Haskell as Donna
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