A question with a lot of confusion is why players can’t keep rolling their skill checks until they succeed. In my opinion there can be three reasons. You either ruin the opportunity, you only have time for one try or you believe it can’t be done.
1 – You get one chance
You walk up to an NPC with a cute smile and a wink, and ask them if they want a drink. Unfortunately you roll a 1 on your charisma check and get a drink in the face. The NPC won’t very likely change their mind if you try again with some pick-up line. Just as you won’t win the trust of a guard that saw you stealing, you won’t win the trust of an animal after attacking it and you won’t intimidate a thug that just saw you fumble with your weapon.
2 – There is a limited time window
You hear the patrol guard coming your way and you have one chance to pick a locked door. You either succeed and slip away unnoticed or you fail and get busted which will result in combat. Examples of a limited time window might be: a priceless item which is temporarily not guarded because of a distraction, the catching of a vase before it shatters on the ground or the tracking of footsteps in the sand before they wash away in the rain.
3 – Your PC believes it impossible
You see an old door with a rusted lock and put your full body weight against it, but roll a 3 on your strength check. The door won’t budge and you believe it impossible under the current circumstances so you won’t try again. You might still succeed by trying again with a friend or a battering ram, or after setting the door on fire, but in those circumstances your player might assume they still have a chance. The mindset change also goes for insight checks. When failing to see a lie, you heartily believe the liar to be true.
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