Context: I’m dming for the first time for a group of friends who’ve never played before either, and we decided to do a simple, tutorial-like campaign just to test the waters. The game starts in a prison that they were SUPPOSED to escape from within the first half-hour to get on to the fun part, except that two of the five players got critical failures on their stealth rolls and now the guards are coming.

Rogue: I roll to persuade the guard to fight the other guards

DM (me): I- okay, I mean, you can try but-

Rogue: *rolls a fourteen*

DM (me): …what are you saying?

Rogue: I’m convincing him to fight?

DM (me): no like, what words are coming out of your mouth? You can’t just magically persuade by getting good rolls you need to actually say something to get him to do what you want

Rogue: oh… uh…. I tell him that I have a lot of wealth and money and will give him some if he helps get us out of here!

DM (me): … I’m…. I’m giving you disadvantage on this

Rogue: what? why?

DM (me): you, a bloodied and dirt-covered prisoner, convicted of theft on the outside and then murder once you were already in jail, sentenced to death and caught trying to escape, are telling this hired muscle, this working family man, that you are actually rich, and are trying to bribe him to fight his co-workers to the death. I am giving you disadvantage on this roll.

Rogue: … *rolls a three*

DM (me): the guard swings his sword towards you and strikes you for three damage

Rogue: f&*$