Mariah Carey opened up about her relationship with Derek Jeter in a recent interview, discussing their first meeting and the inspiration behind her songs "The Roof" and "My All." The Grammy winner revealed that the track "The Roof" was about their first kiss on the roof of Jeter's apartment building, while "My All" was about risking it all for a night with the former New York Yankees star in Puerto Rico. Carey and Jeter were linked in 1998, and while they both moved on to other relationships, their brief romance left a lasting impact. Jeter's former teammate recalled a teenage Jeter expressing his admiration for Carey, hinting at a possible future together.