Why do I feel like I'd be the only one to do this in light-hearted jest...? ._.
Because most folks on here want to roast pinkie to see her cry. What they don't know is that I'd take her home and make her feel better.
I'd roast all of the main 6, excluding Fluttershy since she wouldn't be able to take it for a single joke.
The point of a roast is to make fun of people in a horribly brutal way, yet not actually have any hard feelings towards them. If you go to a roast, it's because you agreed to it. You WANT to be made fun of and WANT to hear the jokes that people can make about you.
If people are misinterpreting that, then that's on them because I even defined what a roast is in the OP. It's not supposed to be malicious.
I know. You defined a roast very well in the OP. But I think some people are... not misinterpreting so much as using the roast as a cover for malicious intentions. Luckily, it would only be friends of Pinkie's, in this case, that would be allowed to make jokes.
I'd befriend her quick to get all the info I could use. Then I'd do the same with RD, that'd be SOO much fun.
Those who roast you can be friends, people you've worked with closely, those you have dated, etc. You don't roast them unless they agree to it, meaning that they want to hear what you can say about them. Not every person who roasts someone tells something that is actually true. You can draw from what you know about them, things you went through together, or just make s**t up on the spot. If they get upset, you're the ultimate roast master because they got pissed. Although, they're not supposed to because it's just razzing on one another.
I guess I'd want to get to know them first because most of my jokes are contextually based. If they aren't they usually suck. It'd be like The Situation trying to roast someone; just not funny. I'd have to have RD come save, lol. It would be so embarrassing.