Before her memoir published, Mariah told Oprah about her relationship with Derek Jeter during a September 2020 episode of The Opera Conversation, and she claimed her relationship with the baseball star was the "catalyst" for her divorce from Tommy. In her memoir, Mariah revealed that she and Derek met at a dinner outing and her assistant helped her keep the romance a secret. "I enrolled my assistant," she wrote, per Vulture. "We'd stage an errand and leave in her car, and I would talk to him. Sometimes we would go to her house, and I'd sit in her modest little living room and talk to him in a whisper — I was that afraid of Tommy."
Eventually, she and Jeter had a rooftop date, which inspired her song "The Roof," according to Mariah's August 2020 interview with Vulture. Though it's unclear how long they dated or why they split, it doesn't seem that Mariah has any hard feelings. As she told Oprah, "Honestly, I don't think it was like, 'Oh my gosh, he was the love of my life.' At the time I did, because I didn't think I'd ever meet someone who [didn't feel superior to me]."