For a heartbreaking little vignette I love this Rufus Wainwright song, 'The Art Teacher'. I like it when people sing in character and away from their own gender too, there's something very folk-song about it. I think it stems from when I first heard Dylan's pre-Animals version of House of the Rising Sun and realised he was singing from the female perspective. Anyway, great song...
The Art Teacher
There I was in uniform
Looking at the art teacher
I was just a girl then;
Never have I loved since then
He was not that much older than I was
He had taken our class to the Metropolitan Museum
He asked us what our favorite work of art was,
But never could I tell that it was him
Oh, I wish I could tell him,
Oh, I wish I could have told him
I looked at the Rubens and Rembrandts
I liked the John Singer Sargents
He told me he liked Turner
Never have I turned since then
No, never have I turned to any other man
All this having been said,
I married an executive company head
All this having been done, a Turner,
Now I own one
Now here I am in this uniformish, pant-suit sort of thing,
Thinking of the art teacher
I was just a girl then;
Never have I loved since then
No, never have I loved any other man
https://youtu.be/Zr9NMQx0VzM