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Nerdarchy > Dungeons & Dragons  > D&D Skills 101  > 5 Deception Skill Challenges for 5E D&D
5E D&D Deception skill check Stealth skill challenge

5 Deception Skill Challenges for 5E D&D

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Salutations, nerds! Today we are going to talk about the art of creative truth telling. You know, like a liar. That’s right, today is the day of Deception skill challenges for fifth edition Dungeons & Dragons! As per usual the idea is you can take any of these five skill challenges and seamlessly drop them into your game. They are designed to be isolated incidents but if you want to play them into a larger issue of course you can feel free to do that. Without farther ado, let me tell you where the lies are in 5E D&D.

5E D&D Deception skill check skill challenge Sheila D&D cartoon

Illustrator Robson Michel describes this as a redesign of the Sheila character from the old Dungeons & Dragons cartoon. She’s a thief with a cloak of invisibility. [Art by Robson Michel]

5E D&D Deception skill challenges

Frame Job

Checkpoints are a thing in most cities and this one is no exception. In this skill challenge a guard stops the party in a fairly public place and produces some restricted substance from the party’s belongings. This could be the remains of a monster, some kind of potion or even just a magical object in a city where magical objects are carefully regulated.

Use When. You want to get the point across that a certain kind of object isn’t kosher in the city the characters are in, or that the guards are averse to traveling adventurers.

Result of Failure. Could be as serious as being tossed in jail or as light as having the object confiscated.

He Went Thattaway

An NPC comes through and tries to get the adventurers to lie and say they never saw them when the guards come through. If you make this person comical in some way players are more likely to go along with it when they hides in a giant vase or a nearby wardrobe.

Use When. You want a way to introduce a new NPC in a striking fashion.

Result of Failure. The guard finds the person and either arrests them or they have to keep running. Sometimes the consequences aren’t for the players to bear.

Reason for the Weaponry

A local law dictates you are allowed to open carry whatever you need as long as it’s part of your job, and the job is something that must be done within city walls. The guards have questions about why the adventurers need so many weapons inside city limits. Come up with a reason for the weapons you have on your person.

Use When. You want to bring the feel of a campaign back down to earth a little bit in terms of what is and isn’t allowed in crowded areas.

Result of Failure. The characters might be told to go put their weapons away. With the wrong group however this could easily end in combat so use with care.

That Ensemble

A vain nobleman wants to know if the outfit they’re wearing looks good on them and is well known for throwing fits when they’re told something they don’t want to hear. The outfit looks absolutely terrible. The colors are garish and it fits poorly but they seems incredibly fond of it.

Use When. Characters are trying to get something out of a local rich NPC and you don’t want it to be as easy as walking in, asking and walking back out with it.

Result of Failure. The noble will be offended and they might not get the thing they want.

That Which Chills You

In a moment where the characters are in a room with a shady NPC, potentially a villain or maybe someone they aren’t certain about, there’s a flash of a smile and the NPC asks them what they are most afraid of. If you really want to drive the suspicion up ask for a Wisdom saving against being compelled to answer — but not compelled to answer truthfully.

Use When. You want to set up an NPC as being super creepy and possibly an antagonist, whether this is merited or not.

Result of Failure. This NPC now knows the character isn’t actually afraid of what they said and that they weren’t honest with her. It might lead them into digging up the real answers.

And there you have it. Five lies you can insert into your game as a skill challenge to test characters’ powers of Deception. Of course we all know the dungeon never survives first contact with the players, so if you do opt to use any of these please do let me know how it went for you in the comments below, and of course stay nerdy!

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Robin Miller

Speculative fiction writer and part-time Dungeon Master Robin Miller lives in southern Ohio where they keep mostly nocturnal hours and enjoys life’s quiet moments. They have a deep love for occult things, antiques, herbalism, big floppy hats and the wonders of the small world (such as insects and arachnids), and they are happy to be owned by the beloved ghost of a black cat. Their fiction, such as The Chronicles of Drasule and the Nimbus Mysteries, can be found on Amazon.

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