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Derek Jeter’s Ex-Girlfriend Mariah Carey Once Described How She Carried Her ‘Secret Romance’ With the MLB Icon in Puerto Rico

Published 12/31/2022, 11:30 AM EST

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Derek Jeter swayed the hearts of an uncountable number of baseball fans during his playing days. Just as well, he enchanted a bevy of beauties with celebrity status. But none higher on the popularity level than Mariah Carey. The Jeter-Carey love affair turned out to be a brief romantic fling, but still memorable nonetheless. 

At least, on Carey’s part, it became the most unforgettable experience of her life. Notably, Carey met Jeter while she was still a married woman. But by her own admission, she was in a rather unhappy marriage with music executive Tommy Mottola. So her extra-marital affair with Jeter almost became a sweet escape from the harsh realities of life. Carey was so deeply in love with Jeter that she followed Jeter to Puerto Rico.

Mariah Carey’s narration of her romantic escapades with Derek Jeter 

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Jeter had this vivid dream of playing for the Yankees and eloping with Carey after moving to New York. Interestingly, it all panned out for Jeter almost exactly as he dreamed of. The intimate moments that Carey shared with Jeter on his apartment rooftop inspired her to write two songs. While Carey’s first song ‘The Roof’, described her sensual experience with Jeter, another song, ‘My All’, depicted the whole love affair.

And as earlier mentioned, she even flew to Puerto Rico just for her then-love Derek Jeter. She narrated the same in her autobiography.

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Mentioning the entire tale in her memoir, ‘The Meaning Of Mariah Carey’, Carey wrote, “I was still absorbed in the memory of the roof and wasn’t willing to fall back into the mud of despair. A new part of me was alive, and I was intent on feeding it. I heard from one of the Armani people that Derek was going to be in Puerto Rico. At our next therapy session, I announced to Tommy that I needed to go on a trip.” 

‘It Was So Sensual’- Megastar Mariah Carey Once Looked Back at Time With NY Yankees Legend Derek Jeter as ‘A Short and Sweet Dream’

Carey further wrote, “I made it sound super reasonable: perhaps me and my assistant, or maybe another girlfriend, would go away for the weekend, to somewhere where I could swim in the ocean and chill in the sun and write (keeping in mind I’d never done anything like that while at Sing Sing, never)—somewhere beautiful and close, like Puerto Rico. My assistant was totally into it. She was still young herself, and this was a legitimate secret romance. We were all caught up.” 

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Jeter and Carey broke up in 1998 and traveled on separate routes in their respective lives. But recollections of the affair stayed as fresh as ever for her. So, do you believe Derek Jeter and Mariah Carey would have made a perfect celebrity pairing? 

Watch This Story – From Mariah Carey To Lara Dutta: Derek Jeter’s Star-Studded Dating History 

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Written by:

Madhurjya Bhuyan

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Madhurjya Bhuyan is an MLB author at EssentiallySports. He has a Bachelor's and Master's Degree in English Literature from Gauhati University and IGNOU, respectively, and also possesses prior professional experience as a content developer. Being a performance artist since childhood, Madhurjya has always aimed to contribute towards creativity in any possible manner, and writing only boosts that desire.
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Edited by:

Abhishek Kumar