Darlene "Woo" Barnes [Jada Pinkett Smith] is a gregarious New York woman whose magnetic personality often leaves men tongue-tied and a little swooning. When her psychic friend, Celestrial [Lina Bradford], insists that the man of Woo's dreams is about to walk into her life, Woo remains skeptical, even as Celestrial becomes convinced that Woo is fated to meet a tall, debonair Virgo. The evening of fate arrives just as Woo’s cousin Claudette [Paula Jai Parker] and Claudette's boyfriend Lenny [Dave Chappelle] plan a quiet night together, only to wind up keeping Woo company instead. Lenny reaches out to his best friend Tim Jackson [Tommy Davidson] to take Woo out, but Tim—a shy, rule-bound law clerk—finds himself navigating Woo's bold, brassy energy. The pairing promises fireworks, even before it truly begins.
Things take a wild turn when Lenny and Claudette’s evening spirals: Lenny’s odd obsession with chicken leads Claudette to dress up as a saucy yet awkward “chicken ho,” complete with clucks and struts—until feathers and allergies complicate the joke. Meanwhile, Woo, initially unfazed by the matchmaking chaos, hears that Tim is a Virgo and interprets it as a sign. She decisively heads to Tim’s apartment, certain that this is the moment predicted by the stars.
Tim, buoyed by a flutter of excitement, seeks guidance from his neighbor Darryl [LL Cool J], who supplies him with incense, edible body oils, and a sultry-song tape to set the mood. When Woo arrives, Tim is instantly smitten, but the reality of Tim’s persona—less spontaneous seductress and more cautious, earnest guy—soon becomes apparent. Woo sees through Tim’s practiced cool and tests him with playful taunts, a dynamic that only heightens the spark and the potential for mischief.
The date gains momentum when three of Tim’s buddies—Frankie [Duane Martin], Hop [Darrel Heath], and Romaine [Michael Ralph]—drop in, bringing a boisterous, chauvinistic energy that irritates Woo. She pushes back in a way that unsettles the party and challenges Tim to defend his growing interest. The group’s presence shifts the mood, but it also pushes Woo and Tim toward a real connection, even as they navigate the boundaries of attraction and awkward humor.
Their official date begins at a stuffy Italian restaurant where Woo’s uninhibited persona rubs Tim’s more restrained nature the wrong way, leading to an early ejection. They pivot to a dance club, where the evening escalates as Tim endures a confrontation with Woo’s ex-boyfriend while Woo stands her ground. The night is filled with a string of comic misfortunes—slapstick, close calls, and rapid-fire banter—that ultimately reveal Woo’s genuine desire for Tim. Despite the chaos, Woo reaches a dawning realization that Tim might be the right match after all.
The misadventures thread toward a hopeful close: Tim regains his car only for it to be smashed to pieces in a later twist, and Woo, in a moment of practical generosity, offers to share not just a ride but her life with Tim. What began as a star-crossed, fate-driven encounter evolves into a relationship built on humor, resilience, and a willingness to look beyond first impressions. Throughout, the film anchors its humor in the push-pull dynamic between Woo’s fearless exuberance and Tim’s earnest, careful approach to romance, using wit and warmth to explore how two very different people might discover common ground—and perhaps even love—in the bustle of New York City.
As the night unfolds, the story remains grounded in character—Woo’s larger-than-life charm, Tim’s earnest awkwardness, Claudette and Lenny’s chaotic subplot, and the supporting misfits that color the evening. The mood stays playful yet genuine, inviting audiences to laugh at the chaos while rooting for Woo and Tim to find a shared rhythm. The ending leaves a sense of possibility: that true connection can emerge from a series of imperfect moments, and that sometimes destiny pairs us with the person who can balance our wild edges with a steady, kind presence.
