The singer Ava Cherry was sound asleep in her Lincoln Park home on the morning of January 11 when her phone began incessantly chiming and vibrating with alerts. Who’s Facebooking me and texting me this much this early? she wondered. What’s going on? Clearly something was wrong. She awoke at almost 5 AM to find some 350 messages reacting to the death of her ex-boyfriend and collaborator David Bowie. “My heart just sank,” recalls Cherry, who was raised in Woodlawn. “I felt kind of lonely. I don’t know why I felt that suddenly because, of course, he was married—but my remembering him from the past was just a flood of fantastic memories. He began my career in many ways.”

You grew up in Woodlawn in a working-class family?

What made you so dogged about finding him?

How did your professional relationship turn romantic?

He would look out for me too. We were at an Andy Warhol party once and I was drinking champagne and I guess I’d had too much. He came over from the other side of the room and said, “Ava, don’t drink any more champagne.” I said, “Why?” He said, “You’re getting drunk. Do you want to be in the paper tomorrow drunk?” That stuck with me. When I go to functions now, I don’t even drink.

Was that exhausting—trying to vie with all the admirers for his attention?