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Movies like Woo (1998)

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.