Woo is a woman in control of her world. She is smart, self-confident, sophisticated and snarky. And she doesn't have any trouble attracting members of the opposite sex. But for some reason no one ever sticks around. Woo meets Tim, a paralegal who is her complete opposite. They shouldn't click. However, Woo and Tim begin to bond when a series of weird and stressful calamities hits them while they are on their first date.

Jada Pinkett Smith
as Woo

Tommy Davidson
as Tim

Duane Martin
as Frankie

Michael Ralph
as Romaine

Darrel Heath
as Hop

Dave Chappelle
as Lenny

Paula Jai Parker
as Claudette

LL Cool J
as Darryl

Orlando Jones
as Sticky Fingas

Billy Dee Williams
as Himself