Plot summary

In New York City, 22-year-old elementary school teacher Jack Jericho (Robert Downey Jr.) flirts outrageously with women. He practices his pick-up lines constantly, his favorite being, "Did anyone ever tell you that you have the face of a Botticelli and the body of a Dégas?" He cruises through the city in his vintage 1968 red Chevrolet Camaro convertible, always on the lookout for another conquest, and has no hesitation about double parking on the street when he spies a beautiful lady. He sleeps with many of those women and has the telephone numbers of many more on a sheet of paper that he keeps with him at all times.One night when Jack goes into a trendy club, he sees a beautiful, 19-year-old redhead named Randy Jensen (Molly Ringwald), chatting with Alonzo Scolara (Harvey Keitel), a mob boss owed money by her father. Alonzo wants Randy to sleep with a Colombian drug lord, Fernando Portacarrero (Bob Gunton), who has taken a shine to her. Despite this being a way of reducing her father's debt, she refuses, saying sex and money do not mix.The next day, Jack Jericho spies Randy at an Off-Track Betting office, making wagers on the days horse races. When she comes out, Jack rushes to introduce himself. Randy at first resists his flirtations, but soon is in the backseat of his car having sex. Afterward, when he asks for her telephone number, Randy sees his large list of women's numbers and refuses to give hers to him. Randy gets out of the car and walks to her job at the American Museum on Natural History in Central Park, where Alonzo waits, demanding his money. Jack follows to learn where Randy works, then books a tour of the museum, requesting Randy as tour guide.A few hours later, he shows up with the youngsters on the elementary school softball team he coaches. Randy is chilly toward Jack during the tour, but he keeps pressuring her to have dinner with him. She demands he throw his list of phone numbers away before she will consider it. He crumples the sheet up and tosses it away, but she is not impressed and walks away. He slyly retrieves the sheet and then goes to his friend Phil (Danny Aiello), who owns a local coffee shop. Phil tries to set Jack up with some models who come in, but, surprisingly, Jack is not interested. He returns to the museum at closing time and, unbeknownst to Randy, follows her onto the subway, home to Coney Island.Through the apartment window, he sees Randy arguing with her intoxicated father, Flash Jensen (Dennis Hopper), but assumes Flash is her boyfriend. Jack comes to her rescue, but she gets angry with him for being there. A moment later, Alonzo comes to the door, demanding the $25,481 Flash owes him. To impress her, Jack offers to pay the debt, but she refuses.Later, Jack and Randy go to the Coney Island amusement park, play some games, and get along well. He accompanies her back to the museum, where she picks up her paycheck, but she ditches Jack and gets on a bus to Atlantic City, New Jersey. Jack goes to his friend, Phil, asking for the cash to pay off Alonzo. Phil says he does not have that kind of money, but is impressed that Jack is so much in love.Jack and Phil return to Coney Island, where Jack learns Flash is Randy's father rather than her boyfriend and Flash suggests Randy went to Atlantic City. In Atlantic City, Randy cashes her $525 paycheck and starts playing blackjack. She wins hand after hand until she has $13,000 and unwisely decides to bet it all on a single hand. Unfortunately, she loses all the money and rushes out, devastated. Jack follows her to the boardwalk and suggests she gamble on him. He trades in his vintage Camaro at a used car lot for $2,950.Jack and Randy return to the casino and go to the Roulette wheel, where he bets $1,000 on number 13, Jack's lucky number, and $1,950 on number 11, Randy's lucky number. The ball lands on number thirteen. At 35-to-one odds, Jack wins $35,000... more than enough to pay off Alonzo.When Jack goes to pay off Flash's debt, Alonzo refuses to take the money, preferring Randy to sleep with Fernando Portacarrero. Jack causes a scene in the casino and physically threatens Alonzo until he accepts the money. Afterwords, Jack catches up to Randy on the boardwalk and says he intends to use the remaining $10,000 to buy back his car and give the rest of it to her. However, Randy tells him they should not be together, saying they are both gamblers and cannot live their lives taking risks as they just did. Jack responds that you can only gamble when you have a choice, but he has no choice, because he wants to be with her forever. Randy is unswayed, so Jack tears up his list of phone numbers and throws it into the wind. He walks away but Randy does nothing to stop him.Jack returns to New York City and uses the ten grand to pay the back rent on the apartment he shares with his grandmother. The next day when he leaves for work, he finds Randy waiting on the sidewalk for him, wanting to get back together. Jack feigns having doubts, then agrees to have dinner with her. They two walk arm in arm down the street together.