The Pick-up Artist (1987)

In New York City, Jack Jericho, an elementary school teacher who lives with and takes care of his ailing grandmother Nellie, is a bit of a scammer, most notably demonstrated by how he continually rehearses his corny pick-up line in front of the mirror. Along with his good-looking but slightly broken down vintage red Camaro convertible and his surface charm, Jack scours the streets for attractive women on which to to use his well-rehearsed pick-up line. He asks important questions, such as marital status of his potential conquests, after the fact -- if he asks at all -- and doesn't particularly care about the answers. His pick-up attempts are successful a small percentage of the time, but often enough for him, and he collects his targets' telephone numbers on a well-worn piece of paper he carries around at all times. Jack eventually uses his pick-up routine on two women he spies at a nightclub associated with mobster Alonzo Scolara: Lulu, Alonzo's dumb blonde girlfriend, and nineteen-year-old Randy Jensen, a tour guide at the American Museum of Natural History who lives with her alcoholic father Flash on Coney Island. Primarily by working extra shifts at the museum and gambling, Randy is earning money to pay off Flash's sizable debt to Alonzo, which is imminently due. Alonzo will forgive part of that debt if Randy will have sex with one of his "friends," drug kingpin Fernando Portacarrero, who wants her and no one else, but Randy refuses. Randy is unlike anyone else Jack has ever managed to pick up, as she sees through his shtick. She does hook up with him for what she considers a one-time-only thing, only to escape her problems momentarily,but this results in Jack doing whatever he can to help her in the hope of being with her again, if not permanently. What happens between Randy and Jack -- who is in the dark about Randy's full situation with the mobster -- is affected by Alonzo, who tries to show who's the boss by changing the rules about the repayment of Flash's debt as it suits his whim.