Vanilla Ice isn't the only interesting person Madonna dated. She and John F. Kennedy Jr., son of the former president and Jackie Kennedy, met in 1985 after one of her shows in New York City. Madonna was married to Sean Penn at the time, but three years later she was divorced and bumped into Kennedy for a second time (via InStyle).

There are different accounts of how involved the two really were. A friend of Kennedy's told People that the pair didn't progress much further beyond flirting, explaining, "It was a flirtation, and when other people referred to her as M around that time, just by her first initial, he would say, 'I started that.' He called her M when he wrote or faxed her."

The friend went on to add that there was something between the pair, but their busy schedules kept getting in the way of finding out what that might have been. The friend ultimately concluded that while the two did meet up a couple of times, it wasn't what most would consider a relationship (via People).