"The Art of Woo" was the feature film directorial debut of Helen Lee. After the failure of Lee's previous short film, "Priceless", she was approached by co-producer Anita Lee and offered the chance to direct a feature-length romantic comedy; finding herself depressed by the "heaviness" of "Priceless", Helen Lee accepted. She wrote the first draft in two weeks after watching several "classic" romantic comedies; the speed in writing was caused by her desire to receive a grant for up to C$ 500,000 from the Canadian Film Centre's Featured Film Project (FFP), granted for low-budget films. After approval, they received assistance from FFP member Peter O'Brian to ensure they would finish the film within a year.