In the vibrant streets of New York City, we meet Jack Jericho, a 22-year-old elementary school teacher portrayed by Robert Downey Jr., who has a knack for charming the ladies with his rather audacious flirtations. He often finds himself practicing his unconventional pick-up lines, with his favorite being, > "Did anyone ever tell you that you have the face of a Botticelli and the body of a Dégas?" As he zips around the city in his classic 1968 red Chevrolet Camaro convertible, the thrill of the chase becomes his ultimate conquest. His nonchalance towards double parking speaks volumes of his single-minded desire to woo the next beautiful lady he encounters. He becomes notorious for his romantic escapades, keeping a meticulous list of telephone numbers of all the women he has been with, a continuous testament to his overwhelming success in love… or perhaps the lack of depth in his connections.
One fateful night, Jack's life takes a significant turn when he sets his eyes on a stunning 19-year-old redhead named Randy Jensen, portrayed by Molly Ringwald, in a trendy club. However, Randy's situation is complicated; she is interconnected with Alonzo Scolara, played by Harvey Keitel, a powerful mob boss who is rather insistent that she sleeps with a Colombian drug lord, Fernando Portacarrero. This can potentially alleviate her family's debts, but with a firm resolve, Randy declares that she wishes to keep sex and finances separate.
The very next day presents a twist of fate as Jack spots Randy at an Off-Track Betting office, placing her bets for the day’s horse races. Seizing the moment, he introduces himself, but initially finds his flirtations rebuffed. Yet, Jack's charm works its magic, leading him to a steamy rendezvous with her in the backseat of his car. However, when it comes time to exchange numbers, Randy is taken aback by Jack's long list of past conquests and promptly refuses to share her own digits. As she struts away towards her job at the American Museum of Natural History, Jack stubbornly follows, determined to stay in her life.
After reserving a tour at the museum with none other than Randy as his guide, he arrives with a group of youngsters from his softball team, making her icy demeanor toward him throughout the event even more perplexing. Despite his attempts at pressure for a dinner date, Randy holds the upper hand and challenges him to throw away his women’s list before she would even consider it. With a reluctant crumple, he discards the sheet, but upon observing her lack of enthusiasm, he retrieves it later, hinting at his desperation to win her over.
Seeking advice from his friend Phil, played by Danny Aiello, Jack learns that his infatuation with Randy is clear as he finds himself uninterested in Phil's attempts to set him up with models. Instead, a deeper connection with Randy becomes his sole focus. This leads him to tail her to Coney Island, where he witnesses her conflicting relationship with her father, Flash Jensen, portrayed by Dennis Hopper. This revelation clears the air, as Jack mistakenly thought Flash was Randy's boyfriend rather than the troubled father he is, further demonstrating the layers of their lives.
Jack’s determination reaches a peak when Alonzo returns to demand the significant debt owed by Flash, leading Jack to offer help despite Randy’s protests. A whimsical adventure unfolds when Jack and Randy meander through the Coney Island amusement park, revealing a playful chemistry amidst the complexities of their lives. However, just as Randy receives her paycheck, she catches a bus to Atlantic City, leaving Jack confused and heartbroken.
Desperate to recoup his losses, Jack throws caution to the wind and joins her in Atlantic City, where Randy's gambling runs amok as she turns her modest paycheck into substantial winnings, only to fall prey to the risk of betting it all and losing it in a single hand. Capturing the moment, Jack proposes they attempt their luck at the casino once more, risking his beloved Camaro as collateral for future endeavors.
As the two venture back into gambling, Jack makes a sizeable bet at the roulette wheel, placing his hopes on his lucky number 13. With an exhilarating spin, fortune favors him, netting him enough to cover Alonzo’s debt. His bold act of defiance against Alonzo showcases his commitment to secure Randy’s freedom, culminating in an emotional confrontation where a heartfelt declaration of love emerges.
However, a bittersweet twist awaits as Randy insists they cannot be together, proclaiming their shared penchant for risks could lead to more heartache. In a moment of reckoning, Jack tears up his women’s list, symbolizing his choice to pursue a future with Randy regardless of the odds. As he makes his way back to New York, Jack resolves to mend his relationship with his grandmother by settling their back rent, pondering the nature of love, risk, and desire.
To his surprise, when he steps outside on judgment day, he finds Randy waiting, eager to reconnect. A tentative agreement for dinner lays the groundwork for a new beginning, as the two take each other's arms, joyously walking down the street, filled with hopes and possibilities, a tapestry woven from chance encounters and heartfelt connections.
