Movies like The Pick-up Artist

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 he continually rehearsing 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 women he is attracted to to use his well-rehearsed pick-up line, he asking the important questions, such as marital status of his potential conquests, after the fact if he asks at all, the answers to which he doesn't really care. These pick-ups work a small percentage of the time, which is good enough for him as he collects his conquests' telephone numbers written down on a well-worn piece of paper he carries around with him at all times. Jack eventually uses his pick-up routine on two women he spies at a nightclub associated with who he will learn is mobster Alonzo Scolara. The first is Lulu, Alonzo's dumb blonde girlfriend. The second is 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 through extra shifts at the museum and gambling, Randy is trying to pay off Flash's sizable debt to Alonzo, which is imminently due. Randy is however unwilling to sell her body as Alonzo will forgive part of that debt in return for sleeping with one of his "friends," drug kingpin Fernando Portacarrero who wants her and no one else. Randy is unlike anyone else he's ever managed to pick up, as she has his number down, but does hook up with him for what she considers a one-time only thing if only to escape her problems momentarily. In return, without yet knowing Randy's full story, Jack does whatever he can to help her in his infatuation. What happens between Jack and Randy is affected by Alonzo, who needs to show who's the boss in changing the rules as it suits his whim.