When Sam Baldwin's (Tom Hanks) wife dies, he decides to move to Seattle with his son, Jonah. When Jonah sees how sad his father is, he calls a radio psychiatrist, who dubs him Sleepless in Seattle cause Jonah says he can't sleep. He starts to talk about his wife and women over the country hear his tale and one woman Annie (Meg Ryan) who lives in Baltimore can't help but fascinated by his tale. Annie despite being engaged can't stop thinking of Sam and soon tries to find all she can about she even goes to Seattle to see him. And once she gets off the plane, Sam who was in the airport to see someone off, sees her and can't keep his eyes off her and tries to follow her but couldn't catch her. Jonah who has been going through the mail that his father has gotten ever since he was on the radio, sees the letter Annie wrote on a whim but didn't send it but her friend did. He tells his father this could be it. But Sam doesn't think he could have a relationship with someone who lives so far away.

The Plaza Hotel, 750 5th Avenue and Central Park South, Manhattan.

Tiffany & Co Store, 727 5th Avenue and East 57th Street, Manhattan.

East 35th Street and Madison Avenue, Manhattan.

otsoNY Comments: Initially, the film studio faced a setback when the Empire State Building's management declined to close the observation deck to accommodate filming of the movie's climactic scenes. However, director Nora Ephron, a firm believer in the notion that "you are two phone-calls away from anyone," leveraged her connections effectively. She contacted a publicist who represented Leona Helmsley, the building's owner who was serving time for tax evasion. After a persuasive conversation with her publicist during a visit to the prison, Helmsley agreed to grant the film crew a six-hour window to shoot their key scenes. This critical permission enabled the crew to capture the helicopter shot, Annie’s entrance in the lobby, and Jonah’s poignant search for Annie on the observation deck.

Empire State Building Observatory Deck, 350 5th Avenue and West 34th Street, Manhattan.

Rainbow Room, Floor 64, 30 Rockefeller Plaza, Manhattan.

Queensboro Bridge, East 59th Street (btw Manhattan and Queens) New York.

Rockefeller Plaza, 30 West 50th Street (btw 5th and 6th Avenues) Manhattan.

otsoNY Comments: Meg Ryan, who played Annie, experienced physical discomfort while filming her frantic run towards the Empire State Building. The cause was a pair of ill-fitting shoes, which added an unintended layer of realism to her character's desperate dash to meet Sam.

5th Avenue (btw East 33rd Street and 34th Street) Manhattan.

Empire State Building Lobby, 350 5th Avenue and West 34th Street, Manhattan.

otsoNY Comments: For the pivotal scene where Sam and Annie finally meet, the observatory of the Empire State Building was too logistically challenging to use. Instead, a detailed replica of the observatory was constructed inside Hangar 27 at Sand Point Naval Base. The building was then digitally enhanced to mimic the New York City skyline at night, adding to the scene’s romantic ambiance.