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A year after Coreen left him, Sidney is still heartbroken,unable to forget her. Deciding he will give his love for her a last chance, he sends Coreen an airline ticket, asking her to meet him in New York City at the top of the Empire State Building. To make sure he completely depends on Coreen’s will to reconnect without knowing whether she will come or not, he throws his cell phone into the ocean and begins his journey, without a backup plan.

Sidney travels from his native Florida to New York a full day earlier to kill some time waiting for the time he’s supposed to meet Coreen. At a coffee shop in Greenwich Village he meets Amy, who’s sharing the table. Having not much to do, the two strike up a conversation.

Sidney learns that the very same morning Amy walked out and left her long-distance boyfriend Michael. Despite not wanting to admit this to herself, Amy has been struggling with their relationship, hoping things would improve. Amy tells Sidney that this is the morning she finally gave up and packed her g. Like Sidney, she now has 24 hours in New York before her plane leaves for San Francisco.

Continuing their conversation, walking through a beautiful New York, they talk about relationships, love, expectations and life. Looking for answers on why he is waiting for Coreen and why Amy has left Michael, Sidney slowly realizes that after spending the day together, he is no longer sure of the things he thought he desired. New York Waiting is a story of a first meeting and a second chance.