In a 2015 interview, we asked Jeff Trott, Crow's frequent songwriting collaborator and guitarist, to weigh in on the mystery. He said:
"I've never ever talked to Sheryl about it – never, ever. One of these days, I'm just going to like throw it out there. Everyone just assumed it was Eric Clapton, but I thought it could be Jakob Dylan from The Wallflowers. The Wallflowers supported Sheryl Crow when I was in her touring band.
But she dated Eric Clapton for a little while, for about six months … But he was really into Sheryl, big time. I thought for sure they were going to get married. I think the real deal is that he really wanted to have a very traditional marriage, meaning that Sheryl would take care of things, in a traditional housewife role. At the time, this was like when she was pretty much peaking and playing everywhere, and she would've had to give that up." (Here's the complete interview
with Jeff Trott.)