In 1938, a waiter working in the Chrysler Building's Cloud Club, which is 66 flights high, observes the hustle-and-bustle of Valentine's Day in New York City. Compared to the average New Yorker, the Cloud Club members are wealthy and accomplished businessmen, although the waiter notes that none of them have made a building as tall as the Chrysler. The Chrysler, like other New York structures, is given human qualities -- "she" is feminine, beautiful, and personified as a "doll." 

As the waiter is preparing elaborate drinks for the members' special day, the Chrysler Building suddenly steps off of her foundation and walks southwest towards the Empire State Building. The waitstaff, who are unbothered by the building's movement, attempt to calm down the surprised members. The New Yorkers both inside and outside the Chrysler Building marvel at the sight of the Chrysler walking over to the Empire State Building. The Empire, who was recently built and taller, ignores the Chrysler, which according to the waiter, she is tired of especially since it is Valentine's Day.

When the Chrysler gets closer, the Empire becomes visibly "nervous," as seen in his wobbling and trembling. The waiter claims that the Empire would be foolish if he turns down the Chrysler's advances. When the Chrysler taps the Empire on his "shoulder," the waitstaff take bets on what the buildings will do next.

Finally, after another tap, the Empire walks with the Chrysler, much to the delight of the citizens. The two buildings walk east towards the East River, which causes other structures to talk and gossip about them. The waiter then notices a pretty girl (whom he refers to as a "doll") in the Empire Building looking at him and points her out to other waiters in the Cloud Club. The girl, who is a singer in a band in the Empire Building, begins playing "In the Still of the Night" as the Chrysler and Empire kiss and laugh in the river. The waiter is mesmerized by the singer during the buildings' river romance, and right when the two buildings begin to make love, the waiter tosses a rope across to the Empire side, which the girl takes and ties to her piano. The waiter crosses the tightrope and finally holds the girl in his arms. As midnight rolls around, the waiter contentedly watches the waitstaff and other fellow buildings rejoice.