Madonna and Sean Penn’s Wedding

The courtship had its rocky moments, but friends at the time said their love was the real deal. “I’ve never seen two more passionate people. Forget about the superstar stuff; Madonna is a girl wildly in love,” a friend of Madonna’s told PEOPLE. After the wedding, they had plans to build a spacious estate in Malibu that would be beyond private.

The couple divorced in 1989, though Madonna later reflected on her feelings for Penn in her 1991 documentary Truth or Dare, calling him “The love of her life.” They went on to remain good friends.

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