Thanks for replies...I'm not sure I'll ever feel comfortable with using sing but maybe I'll feel differently when running it.
Why do you feel uncomfortable with it? Is all your RP in the 1st person, so you feel the player has to sing?
You can just go third person, and the player says 'I sing an old song about heroes waking from sleep' and roll the dice.
There isn't any chance of any player having to burst into song!
It's just so strange having to wake someone this way
But in literally the only example we have of this in Tolkien, it's what happens. Tom Bombadil sings a magical rhyme to help them.
People sing a lot. All over the world. And in pre-literate cultures, which are the basis of Tolkien, they have to sing or chant to remember stuff.
You keep saying 'burst into song' like it's a musical and they're going to jump and spin.
In my world, there are often songs. People sing while drinking. Young people and families go to karaoke boxes together. My daughter and partner both often sing. I sing in the shower, or just while walking. Quietly, if other people are around, but I do sing.
It's not strange to sing.