My best friend's daughter irl decided to charm the bugbear guard. I made puppy dog eyes at her while her parents giggled their asses off. She was thirteen at the time.
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You absolutely do not have to RP this. You can say "No." You can say "Ok, you go off and do that, what's everyone else doing?"
Exactly this. I had a character go to a brothel in a campaign I ran. I just said okay, you go to the brothel and have whatever you consider a good time. No further detail or RP was requested or required.
"the bouncer notices you both looking smarmy and throws you halfway across the city as you try to enter, roll for the landing"
Nope, no, that's encouraging their behavior. Now your player thinks you're giving them a quest to thwart this bouncer.
great, what the players don't know is that the bouncer is a trickster god in disguise and they simply will not ever get past him, and they can have fun throwing themselves at a brick wall repeatedly while everyone else carries on with the actual campaign.
Except that's the point, they will not be having fun. Nor will you, nor will any of the other players. Because that setup is not fun. And presumably you're hosting a game for your friends with the intention of everyone having fun, so it's best if you find another tact.
The bouncer is a God. The DC is 500. Crits are the only way through. There's an instant kill atmosphere in the front room that requires all elemental immunities to survive. If they make it past all of that they are disintegrated by the unfiltered visage of a naked god. I hope they brought another character sheet.
Please remember that your DM is a person. They are also playing the game and deserve to have fun, and for their boundaries to be respected. They are not just a physics engine for your shenanigans.
That being said, some DMs in specific groups might be totally fine with this. Just don't spring it on someone without prior discussion and consent. That is (among other things) what session zero is for.
"Roll a constitution based slight of hand check, add your polearm proficiency." ... "You wake up with extra exhaustion and d12 dignity damage."
I did this to my brother in law. He critically failed every single roll I've never seen that many 1's. He woke up married to an "elf" named Ralph and a mysterious -1 to CON that went away next time he drank a healing potion.