Plot
Jack Jericho is a 21-year-old womanizer, who is constantly honing his craft. Driving around the city in a red convertible, he regularly jumps out and charms women wherever he goes. The principal at the school where he teaches reprimands him for hitting on students' mothers.
Outside of a club, Jack hits on Lulu, who is waiting in her mobster boyfriend Alonzo's convertible. Alonzo comes up and threatens Jack, who goes inside. Mobster Fernando insists he wants Randy, a young redhead in the bar who is getting noticed by many, including Jack.
Lulu follows Randy into the restroom, trying to convince her to go out with Fernando. Randy refuses, and points out Lulu should not be doing his dirty work. Outside, Lulu argues with Alonzo, who decides to leave her there. Jack sees this, offers her a lift and later a cop interrupts them as they are necking.
The next morning, Jack helps his grandmother at home with her insulin. On his way back out, the landlord reminds him the rent is overdue. Seeing Randy in the street, she surprises Jack by agreeing to have a quick fling in his car, but refuses to give him her number. He follows her to work, seeing her being harassed before heading in.
Jack discovers that Randy Jensen is an independent museum tour guide who beats Jack at his own game. Randy's indifference only causes him to become smitten with her. Jack books a tour with one of his school groups, so he can continue flirting. Randy is too busy for romance, trying to keep her alcoholic gambler father Flash Jensen, out of harm's way.
Jack follows Randy to her apartment, pleading, as he cannot stop thinking about her. Alfonzo and his goons then arrive to demand over $25,000 she owes them. Randy is reminded about the offer to have the debt forgiven if she spends the evening with mobster Fernando, but she again refuses. Randy has until noon the next day to deliver the money. Jack offers to help her, to no avail.
They go to Coney Island and Jack tries to win her a prize shooting baskets but fails. They go the museum's planetarium where Randy works to get her pay check. They both go in to watch the show. There, Randy says she is going to be right back, but actually leaves.
Randy gets on a bus for Atlantic City unbeknownst to Jack. She starts up a conversation with fellow passenger Harriet, who talks about her long string of failed relationships. Randy suggests she keeps her interaction with men casual, so she cannot get hurt.
Going to his friend Phil's cafe, Jack tells him about falling for Randy and the $25,000. They go together to see Flash, trying to find her. Realising she has gone to Atlantic City, Phil drives them down. Just as they arrive, Randy is at the brink of winning all they need at black jack. Overhearing a couple of mobsters talking to Flash, Jack realises she is his daughter and not his girlfriend.
Alonso was called in by the mobster running the casino, so he is also there and tries to block them from authorizing a large bet by Randy. Her $13,000 bet does not pay off. Jack catches up to her, and convinces Randy to let him help her. He sells his car for a little over $2,000, and after eating, they return to the casino. Playing the roulette table, Jack wins $35,000 which he uses to pay off Alonso.
Although Jack has freed Randy and Flash of their debt and declares he wants them to be together forever, she insists they are bad for each other. He tears up his sheet of women's numbers and walks away. Back in NYC, Jack pays the missing two months' rent, then encounters Randy outside. She invites him to dinner and they walk off together.
