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| Jada Pinkett Smith | Woo |
| Tommy Davidson | Tim |
| Duane Martin | Frankie |
| Michael Ralph | Romaine |
| Darrel Heath | Hop |
| Dave Chappelle | Lenny |
| Paula Jai Parker | Claudette |
| LL Cool J | Darryl |
| Aida Turturro | Tookie |
| Lance Slaughter | Lamar |
| Dartanyan Edmonds | Shakim |
| Foxy Brown | Fiancée |
| Sam Moses | Cabbie |
| Tiffany Hall | Denise |
| Girlina | Celestrial |
| Billy Dee Williams | Himself (uncredited) |
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.
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