Okay, so this is a story from my senior year in Highschool. I liked to think I was quite the prankster (Spoiler Alert: I wasn't). Occasionally, though, I had my moments. And by that, I mean that I made everything really awkward for an extended period of time.
This story is one of heightened awkwardness.
I was in my 1st Period Seminary Class, and our teacher was taking role. He was great about engaging people in with this, but I enjoyed messing with these sorts of situations. Once, when asked who I was supporting in the upcoming BYU vs U of U Football Game, I said USU (a completely different, uninvolved school).
This instance, though, we were asked who our favorite Disney Princess was. We got simple answers like "Cinderalla, because she has a pretty dress", "Bell, because she likes books", and "Pocahontas" (This individual liked to ruffle a few feathers whenever possible, but we'll get to them later). We even had a well thought through answer of "Rapunzel, because she's independent, but doesn't have Stockholm Syndrome like Belle." (Shots fired!)
Because my last name is towards the beginning of the alphabet and that was the order we were doing stuff in, I had minimal time to figure out how best to troll these individuals. So, my mind rushing to find a suitable inappropriate answer, I asked the fated question "Does it have to be a Disney Princess?"
The teacher, not expecting my hilarious antics, agreed to let me choose another Princess, imagining something profound. Instead, he got the answer "Well, I've always thought that Princess Diana was pretty attractive."
Cue awkward 45 seconds of silence broken only by the groan of my fellow classmate who was familiar with my antics.
"Okay, moving on." was all he could think of. I don't think it's been talked about very much since then.
Now, for most of my classmates, the inappropriateness went way over their heads, since they recognized the name but couldn't place a face or anything. Pretty only my Teacher and two maybe three others understood the reference, making the awkwardness even more profound, since the others knew it had to be something bad, but not knowing what it was or how to react.
For all you scratching your heads at home, Princess Diana was British Royalty for a time. She's dead now. She was married to Prince Charles, and was part of one of the biggest British Scandals and her death was one of the biggest and longest lasting Conspiracy Theories of the 90's. It's still a sore subject for many people (even here in America), so it made for quite the inappropriate joke for those who understood it.
Anyhow, if you want to get sucked into the conspiracy, look it up on Wikipedia, then follow up on Reddit boards, and eventually you will be linked to the most ridiculous explanations ever. Good luck keeping your sanity!