One of the best things about tabletop role-playing games is just how much versatility a player has in any given situation. Any good GM should be able to accommodate any reasonable request from their players, but the real fun come in when a player completely sideswipes you with some genuine shenanigans. Having to adjust and improvise on-the-fly is an absolute thrill that really tests my abilities to honor the request of the player while adhering to the rules and story. It’s a tough thing to develop, but it’s a necessary skill to have when running a game.
During one of my first ever games I ran, the first thing that a player of mine did was just say they were doing something, which in this case was taking a pouch of gold off of an NPC. My first reaction was to prompt them for a sleight of hand check which seemed pretty reasonable in my mind, but then they clarified and said “no, I’m just taking it.” They made it clear that there was no intent for being sneaky or surreptitious at all, they just literally wanted to take a thing that belonged to another character without any resistance. Knowing what I know now, I shouldn’t have relented and instead made them roll a contested strength check or just tell them that wasn’t going to fly without a check, but when you’re starting out you just want to please everyone and let them run free.
Don’t do that. While it may seem counterintuitive to tell your players they can’t do something, sometimes you need to remind them that TTRPGs, while a great forum for wild improvisation, are by and large very rules-heavy games. It isn’t about just saying “no” to your players, rather you need to refocus their energy so they can work within the guard rails of whatever system you’re playing. Saying “no” repeatedly to a player might result in them just checking out entirely or feeling as if they’re being picked on, so usually I try to encourage my players to try a different tactic or work with them to accomplish whatever ridiculous thing they’re trying to do.
Because I play with my friends, there’s a built in level of respect between all of us. They know that I’m trying to give them as much flexibility as I can without completely throwing out the rule book, and I know that they’re going to respect me when I tell them that there’s going to be a couple of extra steps required in the insane shit they’re trying to pull off. I ultimately want their characters to succeed in whatever they’re doing, but that doesn’t mean I have to make it easy on them and let them dictate what rules are and aren’t enforced.
There are plenty of ways that you can help work with your players to accomplish their goals, but for my money I’ve found that just asking my players if they have any abilities that would aid them in their wild requests is something I’ve found not only reinforces the rules of the game, but makes sure they’re paying attention to their character’s unique abilities. But lets say you wanted to be fun for once in your life and just let the players have a good time, well that’s when luck checks, high dice checks and even some deus ex machina can help you loosen up.
Honestly, that’s kind of the secret. If the players want to do a near impossible thing, let them try it and set the DC at 30 and give them disadvantage if you have to. They’ll probably fail miserably if they actually try which could lead to even more hilarious situations. Or maybe they’ll succeed, which might ruin an encounter, but it’ll be a moment they talk about forever. In my experience, I’ve never been so happy to get fucked over by the dice thanks to a rogue natural 20, because the players eat that shit up.
Allowing your players to try something rather than just shutting them down is something that I truly believe you have to do in order to foster a positive gaming environment. If you don’t let your players have fun, they’ll eventually stop caring and stop playing, but if you let them get away with anything then you’ll probably want to stop playing. Having been on both sides of that divide I can attest to how difficult striking that balance can be, but I assure you that striving for that balance is well worth the effort.