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Just started DMing, and in a moment of hubris had a NPC challenge the party to a game of cards… which one of the PCs was proficient in. When asked the reasonable question of "ok what now," I realized I had no idea and a quick skim of the DM guide and PHB (and a longer look later) revealed nothing. Something that could have been fun and a nice character moment turned into a "sorry guys, let me just throw something together and move along."

Are there rules in 5e for what rolls/checks/contests are necessary or expected when using a gaming set? When and how would proficiency come into it? What other skills and proficiencies could come into play (ex: a sleight of hand check to cheat at cards)?

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Welcome to! The [rules-as-written] tag was removed because it's specifically used to indicate that you're only interested in strict literal readings of the rules. If that's the case, go ahead and add it back in. – BESW Feb 19 at 8:31
This question… might also be interesting – Yotus Feb 19 at 9:00
Reminder: comments are for clarifying content, not posting small or incomplete answers. Please use answer posts to submit answers instead. Prior comments containing answers have been removed. – SevenSidedDie Feb 19 at 18:55

The use of the various types of tools (including the Gaming Set) do not rely on a particular skill but instead simply use an ability score appropriate to what you are trying to achieve.

From the first paragraph on p. 154 of the PHB:

For Example, the DM might ask you to make a Dexterity check to carve a fine detail with your woodcarver's tools, or a Strength check to make something out of particularly hard wood.

Having proficiency with a particular set of tools allows you to add your proficiency bonus to the roll in addition to the bonus (or penalty) granted by the ability score that is being used.

As for how the situation would play out, p. 174 of the PHB describes how to handle a contest between two individuals:

Both participants in a contest make ability checks appropriate to their efforts. They apply all appropriate bonuses and penalties, but instead of comparing the total to a DC, they compare the totals of their two checks. The participant with the higher check total wins the contest. That character or monster either succeeds at the action or prevents the other one from succeeding.

If the contest results in a tie, the situation remains the same as it was before the contest.

In your particular case it would depend in part on what game they are playing and what sort of approach they are taking. They could maybe use Charisma to try and bluff their opponent. Or they could try and read their opponent with an Intelligence or Wisdom check. Maybe even Dexterity to try and discreetly slip a winning card into their hand.

Participants do not have to use the same ability check: the NPC could try to bluff the PC with a Charisma check while the PC tries to read the NPC with Intelligence.

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Thank you for a quick and definitive answer. – partywipe2electricbugabearaloo Feb 19 at 19:51

Here are the rules from the PHB p.154 concerning gaming sets:

If you are proficient with a gaming set, you can add your proficiency bonus to ability checks you make to play a game with that set. Each type of gaming set requires a separate proficiency.

It is not specified which ability checks you could use, but Sleight of hand (vs Perception, most likely) would probably be a good one for card games, for example.

Another example: in a bluff game (like poker), you could use Deception (vs Insight) and add your proficiency bonus if you are proficient with this particular game.

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Also, if you play without cheating or bluffing, I'd say it's straight up intelligence. – Diego Martinoia Feb 19 at 10:14
You could also use straight Diplomacy in many games, to manipulate players into being overly cautious, or overly risky with their bets. – lithas Feb 19 at 15:27

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