Set over the course of one day in New York City, the musical takes place after the death of a wealthy man who leaves his fortune to whichever relative has never been in love and never been kissed.

[1] Watch Your Step was Irving Berlin's first musical, and it marked the first time a Tin Pan Alley composer moved "uptown" to Broadway with a complete score.

The songs "Play a Simple Melody" and "They Always Follow Me Around" as well as "When I Discovered You" and "The Syncopated Walk" were introduced by this musical.

[1] The Broadway premiere, produced by Charles Dillingham, opened at the New Amsterdam Theatre on December 8, 1914.

It ran for 175 performances and featured in the cast Vernon and Irene Castle, Frank Tinney, Elizabeth Murray, Harry Kelly and Justine Johnstone.