34. Madonna and Sean Penn
Movie: Material Girl
Location: Hollywood, California
Year: 1985
Madonna and Sean Penn started dating in the mid-1980s after the two met on the set of Madonna’s music video for her hit single, “Material Girl.” The actor and the singer had both just gotten out of relationships at the time, and they weren’t looking for anything serious.
They remained friends, but their friendship soon became a full-on romance. They got married four years after meeting, but the marriage didn’t last. Madonna filed for divorce twice, and the second time, in 1989, the divorce stuck. The Material Girl cited “irreconcilable differences” between the two, putting an end to a tumultuous, tabloid-frenzied relationship.
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