Nick and Jane (1996)

With nods in direction of Picture Perfect and Pretty Woman, this romantic comedy opens with classy corporate executive Jane (Dana Wheeler-Nicholson) discovering her boyfriend/colleague John (John Dossett) in bed with another woman. Exiting into the New York night, she grabs a rundown Checker cab, driven by Nick (James McCaffrey). Jane's friend Vickie (Lisa Gay Hamilton), who thinks Jane should make John jealous, hatches a plan that would give taxi-driver Nick a fake executive background with an alias, "Nolan Miller." Falling for this, John suggests Jane invite Nolan to the annual company luncheon. Jane promises Nick an easy $1500 if he will go through with the charade, and he agrees. Then comes the gender-switch on Pretty Woman as Nick gets a Madison Avenue makeover. By this time, naturally, Jane is realizing she's attracted to Nick, and events become triangulated.