Most people think they have Vonda Shepard's "Don't Cry Ilene" figured out. Most people are wrong. The singer explains in a Songfacts interview:
"Yes. There was a real Ilene. And you know what's funny, it is like documented fact that the song is about an interracial relationship; that's not true at all. I don't know who made that up. It's not about that. It cracks me up, because people say it, like, you know, very educated, interesting smart people think that's what it's about."
So what is the song really about? Shepard says it was inspired by a guy she was "kind of in love with" who already had a girlfriend. (Here's the full Vonda Shepard interview