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I have a player character that got so good at bluffing as a child he doesn't realize he's doing it; as such, the player is wondering if this can let him avoid having to make Deception checks since he truly believes what he's saying.

Here's his backstory:

10 years ago, when Andrew was just a young lad, he went to a bar on not necessarily the best side of town for his kind. He was just a young street urchin who didn’ know anything. He got harassed by some older university students; they started asking him really hard questions. Then he was asked one question which stuck out: "What are your thoughts on the demise of the Georgian empire?" Eager to impress, Andrew gave an explanation using big words he didn’t understand; none of them understood the words either, but didn’t want to admit it, so they said, "Okay, cool." They then asked a much more difficult question, to which they got another response with a lot of difficult words. Still not wanting to admit they didn’t understand, they asked a much more difficult series of questions; they didn’t understand those insights. Little did they know Andrew didn’t understand either.

Many hours and drinks later, Andrew had finally earned their trust and friendship and was invited to sit in some classes with them, at which point he had become adept at giving nonsense answers that sounded realistic. A professor asked a really difficult question that no one could answer, then called on Andrew. Andrew gave the most bullshit answer ever, but the professor didn’t understand; not wanting to look a fool, the professor eventually hired Andrew as his apprentice, and through a series of events, Andrew later graduated with honors from that university.

And here's the request: He doesn't make Deception checks because he doesn't know that he's bluffing. Is this possible by the rules?

Does a character who believes what they're saying have to make Deception checks?

Andrew knows he's bluffing

Your overall question is very interesting: does a person need to make a Deception check if they believe what they are saying is true? I would say "no." In that situation, the person would need to make a different check (likely Persuasion) to convince others of what they are saying, even if what they are saying is false. For example, an indoctrinated cult member who believes that a ritual which will summon his deity will bring lasting peace and prosperity to the world might use Persuasion to sell others on this idea (even though in reality, unbeknownst to him, the deity will destroy the world once summoned).

But "Andrew" in your example knows he's not telling the truth.

As you mentioned in your example, Andrew doesn't know what he's talking about. Andrew gave answers "using big words he didn’t understand", and gave "the most bullshit answer ever." He didn't know what his answers meant, and he knew that he didn't know what his answers meant. He may have believed that his answers turned out to be correct based on everyone else's responses, but at all times he knew that he didn't know what the answer was supposed to be.

Andrew may believe that he's so lucky his answers will always be right, but that's part of lying: believing that you are so slick you can convince anyone of anything. He may believe that everyone at the college is doing the same thing he is (and he may be right). But both of those things are different than saying he believes he actually knows the answers (which he doesn't: he doesn't even know what the words he's using mean).

Let's say that Andrew says something like "Applying any singular cause to the Georgian crisis is postmodernly reductionist, and the height of all antiquarian thinking." Andrew is being deceptive about something. He's not being deceptive about the truth or falsehood of his statement: in fact, he has no opinion on that matter (since he doesn't know what he's saying, he can't possibly have any belief about whether it's true or not). But he's still lying: his lie is that he understands what he's saying (and that if you don't, it's your own foolishness at fault). And for that, he needs a Deception check.

He doesn't make Deception checks because he doesn't know that he's bluffing. Is this possible by the rules?

I would like to answer this with a more general observation, since the specific case of rolling for Deception is covered really well in another answer. As DM, you are free to agree that narratives in the game lead to requiring dice rolls to resolve them or not. A character's backstory is one key narrative in the game. If the backstory said the character had an uncle Jack, then uncle Jack exists, you typically would not roll dice for that. However, if the backstory said that uncle Jack was terribly fond of the PC and also a powerful and extremely rich wizard, then accepting it at face value would lead to discussions of what equipment and support magic the PC could expect during an adventure.

This situation is not much different. I am not sure how the DM or the player has framed background generation, but this player obviously feels that it is OK to ask for a mechanical benefit for the character purely from writing the backstory. In more free-form games this would be fine, but in D&D you are stepping outside the game basics, and opening yourself up to a different game. That is a game where social and creative manipulation of the DM is within bounds, and finding the sweet spot of requests that seem reasonable but still allow automatic success (where other PCs would require a roll) or some other benefit.

In this case, the back story is still fine IMO. A fun and detailed backstory is a great place for a DM to find plot hooks and characters that are meaningful to the player and help create a unique game world that would not exist otherwise.

What the player should do:

• Choose 5E Background options for Andrew that grant proficiency in Deception to represent their particular style of silver tongued glibness. They should expect to roll for Deception as normal (which is to say whenever the DM determines it would be required to achieve an effect - the rules are looser on this than on combat). The Charlatan background is a pretty good match.

What the DM could add to the setting:

• A confused (at least regards to Andrew) and socially awkward professor




• Some contacts from the university (who may be in other local positions now) that think Andrew is some kind of incomprehensible genius, thus could solve anything.




• One or two university rivals who may or may not be taken in by the arcane gibberish that Andrew is prone to spout, but who have some kind of axe to grind over his success. For example, another potential apprentice who was overlooked because Andrew took his/her place.