The “Tom’s Diner” of the song is Tom’s Restaurant in New York City, a diner on the corner of Broadway and 112th Street. Singer and songwriter Suzanne Vega was reputedly a frequent patron of the eatery during the early 1980s when she was a student at nearby Barnard College. The mid-twentieth century diner would later become famous as the location used for the exterior scenes of Monk’s Café in the popular 1990s television sitcom Seinfeld.
The song begins with the narrator stopping at a diner for a cup of coffee. The song mentions reading a newspaper as well as seeing two women, one who enters the diner and one who stands outside in the rain. The ringing of bells at a nearby cathedral causes the narrator to reminisce about an unnamed companion and a midnight picnic. At the end of the song, the narrator leaves the diner to catch the train after the coffee is finished.
Vega wrote the song based on a comment by her friend Brian Rose, a photographer, who mentioned that in his work, he sometimes felt as if “he saw his whole life through a pane of glass, and […] like he was the witness to a lot of things, but was never really involved in them.” She attempted to think and write in this fashion (including a male perspective) while sitting at Tom’s Restaurant. The “bells of the cathedral” that she remarks hearing in the song are those of the Cathedral of Saint John the Divine, located one block to the east. source