My mother (born early 1940s) told me that she sang “My Buddy” – music by Walter Donaldson, Lyrics by Gus Kahn – in elementary school. It is considered a World War I song – I have a nice “straight” rendition on a CD entitled Over There! Songs From America’s Wars, sung by Jon English. Actually, it was released in 1922, but it certainly seems to draw on the grief felt over the loss of so many young men in that war. Some people interpret it as sung by a man over his lost war comrade; but to me, even though it has been sung by many male singers, it sounds like the thoughts of a young woman missing a man who’s gone off to war – though possibly more of a “crush” than a full-fledged romance. My interpretation is supported by one of the early sheet music illustrations.
Here is a version by the Canadian singer Henry Burr:
My Buddy
Life is a book that we study.
Some of its leaves bring a sigh.
There it was written, my Buddy,
that we must part, you and I…
Nights are long since you went away.
I think about you all through the day,
My buddy, my buddy,
Nobody quite so true.
Miss your voice, the touch of your hand-
Just long to know that you understand,
My buddy, my buddy,
Your buddy misses you.
Buddies through all of the gay days.
Buddies when something went wrong.
I wait alone through the gray days,
missing your smile and your song…
Nights are long since you went away.
I think about you all through the day
My buddy, my buddy,
Nobody quite so true.
Miss your voice, the touch of your hand-
Just long to know that you understand,
My buddy, my buddy,
Your buddy misses you.

This rings true. My grandparents were courting in the early ‘twenties and in their earliest letters sometimes called each other “buddy.” “Pal” was used the same way–as in, for instance, the song “Darling Pal of Mine.”
Will, thanks for sharing this. Interesting that these words became more “masculine” later. Also, I think it was quite common to sing a song written in the voice of the opposite gender.