achievementtooth:

You know what drives me crazy? Seeing all these D&D stories that were like “Well, I rolled a nat 20, so the DM couldn’t say no.” I don’t like it, cause that’s not how the system works.

A nat 20 gives you the best possible outcome in this situation, or the best result your actions can give you. Just because you got a nat 20 doesn’t mean you can kick down a heavy steel door, but you could jar it and discover a weak point that was cleverly hidden. A nat 20 doesn’t mean that you immediately make someone fall in love with you by trying to seduce them, especially if it’s a character or creature who’s not prone to getting involved with people like that, but you might endear yourself to them or make someone willing to hear you out. A nat 20 won’t let you jump a gap that any living being is physically incapable of jumping, but you could make it far enough to reach a small and safe outcropping somewhere in the middle.

I don’t know, it just annoys me that a nat 20 is kind of a game-breaking solution to everything at this point. As a DM, it’s frustrating because players expect anything to work if they just roll a 20, but that’s not always the case. It will get you the best result at the time, but the best result isn’t always what a player wants it to be, and it also may not always be what they expect. And it’s often more fun if a roll like that isn’t just an immediate, world-shattering success, since there’s so much that can be done with it.