“I thought, O.K., this is a big decision-making point — because last night was great and do we go forward like we’re dating? Or do we go forward like we’re still just buddies and last night didn’t really have the import that it might have had?” she said.

“And I was a little skittish because I thought, you can’t screw it up with somebody who has been your friend for 25 years. You don’t want to rashly go into something that you’re not sure about. But at the same time, how can you be sure at that moment? So we sort of just went forward as if we were pretending we were dating.”

By the end of their stay in Chicago, Mr. Brakeley was mapping out opportunities to meet months in the future. “And I was like, ‘Whoa, hold on, buddy. I’m not sure I’m willing to commit that far out,’” Ms. Graham said. “Because first of all, he was separated for over a year but he wasn’t completely divorced yet, and he had two little kids. And I guess I didn’t know what it would feel like to be full-stop in a bona fide relationship.”

But she also realized that she didn’t want to lose him again, and decided to take the leap. With their mutual passion for music and theater as well as an understanding of the stress that accompanies a major career, they found that their lives blended seamlessly. And on the rare occasion when she acted the diva, he sweetly reminded her that he had worked for Michael Jackson, who was an even bigger star than she was.

Two years later, it was Ms. Graham who sought a commitment and Mr. Brakeley who was reluctant to give it. But when it became clear that they were going to be together, with or without marriage, she made peace with their arrangement.

“I always wanted to get married sometime, but I never was in the right place at the right time with the right person to do it,” she said. “Once I found him, I thought, this is the right place and the right time and the right person, but he has to want it, too.”