“Will You Be Loving Another Man” is credited to Bill Monroe and Lester Flatt. Monroe’s Blue Grass Boys recorded it on 17 September 1946 at WBBM Radio Station in Chicago, the day after they cut “Blue Yodel No. 4” there. Lester Flatt sang the lead with Monroe on tenor, and the band was Monroe on mandolin, Flatt on guitar, Earl Scruggs on banjo, Chubby Wise on fiddle and Howard Watts (“Cedric Rainwater”) on bass. Columbia issued the two songs together on a 78 in July 1947, with this one on the B-side.
The singer is the one leaving. He is bound for some other land, and he asks his sweetheart whether she will be waiting when he gets back or loving another man. He tells her not to cry on his shoulder and, if he finds she has strayed, not to bother saying she is sorry. The title question returns as the refrain.
The song stayed with Flatt after he left Monroe. He recorded it with Mac Wiseman on Lester ’n’ Mac (1971), and on 18 March 1974 he and Monroe sang it together at Neely Auditorium at Vanderbilt University in Nashville, a performance released on Lester Flatt Live! Bluegrass Festival (RCA Victor, 1974). The Osborne Brothers recorded it at Bradley’s Barn in Mount Juliet, Tennessee, on 8 February 1968, with Bobby Osborne singing the lead, and made it the opening track of Yesterday, Today & the Osborne Brothers (Decca, 1968).