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At the ripe, young age of 56, Madonna can still break the Internet. She confirmed dating Tupac Shakur in the early-to-mid ‘90s, but don’t hold your breath for any details.

Madonna

photo: WENN

Do the dates and details match up? Well, Howard Stern kicked things off by asking her about an interview with David Letterman. In theory, you find the date of the interview and go from there. That’s what we did. With the help of some old press clips and research, here’s a possible timeline of 2Pac and Madonna’s romance.

Photo: WENN

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