Madonna and Michael Jackson, who are both Pop Royalty, have been seen attending events together and spending time together outside the industry.

During the 90s, Michael Jackson and Madonna attended the Oscars together, when she was in the movie ‘Dick Tracy’.

She said back then about the appearance, “Michael [Jackson] was like, ‘Well, who are you going to go with?’ I looked at him and said, ‘I don’t know. You want to go? And he said, ‘Yeah that’d be great’. And then, he took me home. You wanna know what happened after that? I’m not gonna tell you.”

Many fans wondered if Madonna and Michael Jackson had kissed. During an interview in 2016, Madonna said that they had kissed and she was the aggressor.

What was the most awkward date you have been on? Have you been on a first date where the guy wanted you to split the check?