It seems that this argument is just going round and round in circles. The simple answer is - the game provides the basics, the rest is up to the DM.
In a recent combat our rogue player decided he wanted to try to intimidate a Chain Devil... he portrays the rogue as a slightly built human aged 19 who looks younger than he is. The party refer to him as 'The Boy'.
So 'The Boy' wanted to try to Intimidate a Chain Devil... on a battlefield, brimstone heavy in the air, with squadrons of Manes advancing on a city. I guess he was going to try to make it nervous and back down from combat, but I immediately ruled that would never happen. I allowed him to roll though, a dismal result. Next round he tried again. And again, and again. Then he got a natural 20.
This only succeeded in making the Chain Devil perceive him as a threat and go straight for him. Not the outcome he wanted. The player pulled a face - should I have warned him that might happen - no of course not. Should I have told him the creature could not be intimidated, again, no of course not. Should I have let him continue to roll - of course - he can choose to attempt whatever he wants.
Normally in these situations I think that the scene the DM is picturing is different than the one the player is picturing. Perhaps the player keyed into a particular sentence of your description and was erroneously thinking the chain devil was surrounded by the party and was at a disadvantage or whatever.
In general I assume my players and their characters are not complete morons and have a general idea of the likelihood of something happening. So when they propose something completely idiotic I first check to make sure that we're both on the same page as opposed to grinning at their ineptness. The vast majority of the time it is a misunderstanding that is at least partly my fault in how I choose to convey some bit of information. Continuing to ask for rolls just feeds that misunderstanding in my opinion.