Although he later draws back from saying which songs are "true", Stephin says in the booklet that All My Little Words is one of his "true" songs, and that the word 'unboyfriendable' was used by one of his boyfriends in circumstances comparable to those in the song.
LD Beghtol, who sings the song, describes it as a 'neo-Glen Campbell country ballad' [source].
LD writes further:
I sang this in one take. Stephin was covertly taping what I thought was a rehearsal take at my first afternoon in his old studio/apartment on East 5th Street. We finished what I though wa just a run-thorugh and I was all ready to do a real take, but he said: "No, that's it, I think. Listen back.” He did a play back and fiddled with the EQ a bit, but what you hear is what we did.
I was astounded it had come out so well, because Stephin had just given me the rehearsal tape (the basic guitar and piano tracks) to learn it from the night before. And I was so nervous! But I think the note of desperation helped, ultimately. All the other instruments were recorded after my vocal. Claudia always teases me about this song being the only country song ever recorded with crisp, classical diction.