Stern had never heard about their romance, while Madonna said she thought it was public knowledge.
An unauthorized 2007 biography called claimed the two briefly dated one year before Shakur's death.
She's one of the most famous women in the world, but even Madonna has her secrets.
Luckily for listeners, the "Living for Love" singer was in a sharing mood when she appeared on Howard Stern's Sirius XM radio show Wednesday.
At one point during their 83-minute conversation, Madonna revealed that she once dated rapper Tupac Shakur.
"I was madly in love with him, totally smitten," she said. The songs he sang were not childlike at all." Madonna later got the opportunity to meet with Jackson early on in her career, and recalled her very first encounter with the singer."He was famous since he was a child and didn't really have a childhood. She was told her career was "over" after performing "Like a Virgin" for the first time.