In 1985, as Madonna's star was on the rise, she met actor Sean Penn. The couple were introduced when Penn stopped by Madonna's "Material Girl" video shoot and the two became inseparable, marrying months later. But the whirlwind romance was plagued by problems.

Penn had a reputation for losing his temper, especially with the paparazzi. The couple's fame only led to more media attention, which led to Penn punching, throwing rocks at, and spitting on paparazzi. "His temperament is also similar to mine. That doesn't always make for ideal relationships, but I don't know what will happen," Madonna said (via People). Jealousy seemed to be an issue as well, with a source telling People in 1987, "Sean has a lot of insecurities." But Madonna had issues of her own, admitting, "I have my insecure moments and that puts a lot of strain on people. You take things out on the person you love, and that causes fights, alienation, grief ..."

The couple divorced in 1989, but it seems as though the love they once shared is still intact. Madonna and Penn appeared together in 2016 at a charity benefitting Raising Malawi. On stage, Madonna offered to remarry her ex, telling him, "I'm still in love with you," in front of a star-studded audience (via ET). In 2018, Stephen Colbert asked Penn on "The Late Show" to choose between Madonna and Britney Spears, Penn replied, "I love my first wife very much."