5 Intimidation Skill Challenges for 5E D&D

Salutations, nerds. For context, the past few weeks I’ve presented five flash encounters based around a skill challenge you can drop right into your fifth edition Dungeons & Dragons game at any point and aren’t meant to take up too much time or serve as longer plot hooks. The idea is to get dice rolling if things get slow, or stretch to give yourself more table time if players are chewing through your material too quickly (not that that ever happens to me…). I’m moving right along with these flash skill challenges and I realized something very important this week — and event for Intimidation is kind of hard to specify. While there are absolutely situations you can color to make it seem like a deceptive or a persuasive statement are the best way to handle them, typically Intimidation is one of those things either a certain kind of person engages in or one characters reach for as a bit of a last resort. In light of this, instead of coming up with situations only Intimidation works for I’ve gathered up five situations where Intimidation is a valid option and won’t make characters come across like jerks! Let’s get to it, shall we?

The ultimate villain from the old Dungeons and Dragons cartoon from the 80s. Beware! [Art by Robson Michel]

5E D&D Intimidation skill challenges

A Stick Up

Our illustrious heroes are just minding their own business at their favorite local tavern when someone comes in and starts robbing the place. Of course, it doesn’t take a genius to realize the ne’er-do-well’s hands are shaking and their crossbow is only barely loaded properly. They probably wouldn’t be so bold if face to face with someone more skilled than a bartender.

Use When. Discussion at the tavern is starting to run dry or you started them off there and need a way to break the ice.

Result of Failure. Your poor inn keep is going to get robbed and depending on how well the adventurers are known they might get heckled about sitting there doing nothing about it by the other patrons. The bartender might also be pretty mad about the situation.

The End is Nigh

Nothing quite takes the wind out of the sails of a nice day than some poor soul on the street shouting about the apocalypse. This one takes it a bit far, actually going up to people, grabbing them and shouting into their faces. It has to stop, one way or another. And sometimes when you shout into the void, the void shouts back.

Use When. Of course when things are slow at the market but also when you need to foreshadow later use of cultists. [NERDITOR’S NOTE: Cultists make wonderful antagonists. When in doubt, drop some cult activity into a campaign!]

Result of Failure. The zealot is more invigorated in their righteous shouting! The guards are probably going to become involved.

Public Transportation

In this case the protagonists try to use public transportation to get to the other end of the city, whatever this means in your setting. This could be a carriage, a wagon or a subway in a more modern campaign. Regardless, it’s almost at capacity and some bold fool tries to intimidate one of the adventurers into giving up their spot.

Use When. You want to single a character out. Maybe they didn’t get to do much in your last encounter. Players love being picked on and this instance is perfect for this circumstance.

Result of Failure. The rude commuter isn’t intimidated and probably needs punched in the face. Sometimes that happens.

Waylaid

On the road a bandit holds up another group of travelers who aren’t as equipped to save themselves. The adventurers could of course pass them by, but they have the bandits outnumbered by one or two people and they’re definitely better equipped.

Use When. You have the time to actually play out a combat with a couple of bandits because it’s always hard to tell which groups will try to Intimidate and which ones roll for initiative without giving the bandits a chance to back down.

Result of Failure. Probably combat to be honest. It might come to violence anyway.

The Snideness of the Guard

There’s a guy, gal or nonbinary pal watching the door. Who this person is doesn’t matter quite so much as the fact that when you go to enter they block you and condescendingly say you’re not allowed inside. Maybe the quest dictates you have to get in there or maybe your characters just have good reasons for wanting through this door on their own, but either way this guard clearly thinks you’re stupid and isn’t going to let you through. Derisive sniffing is a good indicator that reasoning with this person probably won’t work.

There’s a certain kind of NPC that it’s just incredibly satisfying to watch urine trickle down their leg and see all the disrespect drain out of their face. Really lay it on thick, Dungeon Masters.

Use When. The adventurers are going to see somebody, there’s no combat to get to them but you don’t want it to be as easy as just walking into their office. Also if they could score points with the person they’re visiting by showing they’re scary, even better.

Result of Failure. Make the DC for this one kind of low. If the party whiffs trying to frighten this person into compliance they are probably going to get their skull broken. Which, you know, is also pretty satisfying.

And that’s five Intimidation skill challenges for 5E D&D. Because the adventure never survives first contact with the players, if you do decide to use any of these please let me know in the comments below and as always, stay nerdy!