The film was shot on the streets of New York, capturing the Upper West Side of Manhattan in the late 1980s. The story follows Jack Jerrico, a womanizer played by a young Robert Downey Jr., who meets his match in Randy Jensen — a sharp and independent tour guide played by Molly Ringwald. After a brief fling, Randy's complete indifference changes the game: Jack genuinely falls for her. But Randy has more serious problems — her father, suffering from gambling addiction and alcoholism, has gotten into serious trouble with the mob. Jack, wanting to prove his devotion, offers to help rescue her father from dangerous loan sharks. The film uses many recognizable Manhattan locations on Columbus Avenue and in Central Park to ground its romantic comedy in an authentic New York atmosphere. It's a light but charming 80s romantic comedy that served as an early showcase of Downey Jr.'s natural charisma and rapid-fire delivery.

Filming Locations:

West 73rd Street and Columbus Avenue

In the Movie

Scene where Jack meets Randy on the street at this intersection, tries to charm her with his usual tactics, but she quickly brushes him off and walks away, setting the foundation of their relationship where she is not impressed by his standard moves.

In Reality

The scene was filmed at the intersection of West 73rd Street and Columbus Avenue on the Upper West Side of Manhattan. This corner is in a mixed residential and commercial area, surrounded by brownstones, apartment buildings, and small businesses. It is a busy pedestrian intersection near Central Park, a couple of blocks to the east.

Columbus Avenue between West 74th and 75th Streets

In the Movie

Scene where Jack Jerrico walks along Columbus Avenue and tries out his off-screen lines on passing women, demonstrating his relentless habit of flirting in the bustling Upper West Side neighborhood with typical New York storefronts and pedestrian traffic.

In Reality

The scene was filmed on a stretch of Columbus Avenue on the Upper West Side of Manhattan, with shops, cafes, and brownstones. This part of the street is a typical New York commercial block, especially lively in the 1980s. The area is still popular with locals and tourists strolling through the Upper West Side.