I'm sure she doesn't remember, but one reason I like the song "Chestnut Mare" so much is that the first concert I took my wife to (she wasn't my wife then) was Randy Newman, Richard Thompson, John Hiatt at Wolf Trap Farm Park. Except that former Byrd Roger McGuinn substituted for Randy Newman. And yes, he sang that song.
She was a little skeptical that she could actually like some of the same music and artists that I did. It turned out ok.