Madonna & Sean Penn
What!?! Madonna dated Sean Penn? What’s even crazier is that they were actually married from 1985-1989. Madonna was Penn’s first wife of three, and Penn was Madonna’s first of two husbands. The couple met at Madonna’s 27th birthday party, which is ironic because Penn’s 25th birthday was the very next day.
Madonna’s third album, True Blue, was dedicated to him. She included a note in the album that stated Penn was the “Coolest guy in the universe.” That’s some high school-type romance right there. It must have been a tumultuous marriage because Madonna filed for divorce in 87, withdrew the request, and then refiled in 1989 for good.