The tradition of serenades goes back quite a ways at Otterbein. It was typical that when a couple got engaged the man's fraternity and/or the woman's sorority would provide a serenade. These were very formal affairs. The couple would be present in formal attire while the fraternity and/or sorority would sing senenade songs to them.

Later on the tradition of serenades for engagements disappeared but the serenades themselves didn't; they continued at various random times when one greek organization would serenade others. A fraternity would offer a serenade at each of the women's dorms or a sorority would serenade at each fraternity house. (Sororities didn't have houses in those days.)

Usually the songs would consist of the Otterbein Serenade Medley, the special serenade song of the group, and finally the Otterbein Sweetheart Song. The Otterbein Serenade Medley consisted of a set of standard, popular, serenade songs arranged and pitched so that you could segue directly from one to the next. The Otterbein Sweetheart song was a serenade song particular to Otterbein. It was written by James McCloy, a physics professor, and set to music by A.R. Spessard, a music professor and the director of the glee clubs. The words of the Serenade Medley, and the words and music of the Sweetheart Song, are given below.