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I was not the DM in this session, it was my GF, but she does not speak English so I'm here to ask for all of us. We've faced an issue we can't seem to solve.

It was our 2nd game, no one of us ever played before. We played Lost Mine of Phandelver and finally entered a room with a hostage in a cave. Goblins told that they don't want to fight and proposed a negotiation. We had a jade statuette and one of the PCs told the goblins that we have it (The DM said before that because it cost a lot, the goblins greedily want it).

After that, the goblins asked 20 gold coins and the statuette in exchange for a hostage. Since they had an advantage (3 PCs vs 6 goblins) I told the other players that this is a good price, despite is having to give out almost all our gold, but my friend decided to intimidate them, roleplayed and rolled a natural 20. The DM said that the goblins seemed kinda worried, but since they had a huge advantage, they (only) reduced the price to just the statuette.

After that, my friend was visibly disappointed (and still is) almost to the point where he refuses to play anymore. We were tired at this point since it was our 6th hour or so, and I can understand his mood here.

When we discussed this situation after the game, he explained his point: he had rolled a 20 and this means (in his opinion) that goblins should have released the hostage without demanding any price because it was a 20. I tried to explain to him that it is up to DM to decide the consequences of any actions players do, and in this situation, the DM decided not to give us more. But the player still thinks that the DM was not right in this situation and a 20 is a 20 and he is ready to even have arguments for this game situation. I tried to convince him that the goblins had a huge advantage here and it was not possible that they give us the hostage without any price, but it seems impossible to convince him. He is negative because of the fact that the DM is the final judge and it is the DM's responsibility to decide what happens next.

We've tried to find some solution on what to do in situations like this and did not come to anything.

What can we do?

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    \$\begingroup\$ It might help to provide background on the player's mindset. This mindset of "a 20 means I am a god and I can do anything" is a quite common expectation, although usually unjustified, since most systems do not work like that. Why does the player think that is how the game works? Did he read the book? Is it based on comic memes they saw in the internet? Is it based in some game system they have previously played that actually worked like that? \$\endgroup\$ – HellSaint Jul 17 at 19:44
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    \$\begingroup\$ Welcome to RPG.SE! Check out the tour and the help center to learn more about the site, and you can edit your question to clarify and answer @HellSaint’s requests for clarification. (Also, if you ever need to just talk or rant about gaming and/or players without asking a question here, check out Role-playing Games Chat, usually there’s someone to commiserate with) \$\endgroup\$ – Bardic Wizard Jul 17 at 21:23
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    \$\begingroup\$ Just to be clear: even when talking about other people (that are not present) in chat, we try to not be too harsh or disrespectful. Just so nobody thinks it is okay to rant and insult people in chat. :P \$\endgroup\$ – HellSaint Jul 17 at 21:27
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    \$\begingroup\$ Your question is similar to this one in that the author was also asking about what natural 20s actually mean. Additionally, this question is about how the game would be affected if natural 20s meant a success (and 1s a failure) in every circumstance. \$\endgroup\$ – Greenguh Jul 17 at 23:17
  • \$\begingroup\$ Sometimes a game is only a game. The rules and the dice are to provide structure, not necessarily boundaries. I DM'd once where I was frustrated with the persistent stupidity of the players. It got to the point where they attacked and I was sick of dealing with it, so I stared them in the eyes, rolled the dice, and without looking at them said, "you all died." After a brief argument they realized I had an agenda, too, and it had equal weight with theirs. I also remember setting an expectation where, if they hit 18 on 3D6 they'd get the impossible result. They rolled it, so I gave it. \$\endgroup\$ – JBH Jul 20 at 21:48
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The ruling seems very reasonable

Originally the goblins were at a reasonable advantage and knew it. Successful intimidation made it so they weren't that sure anymore, probably assuming that the PCs were more dangerous than anticipated, making them (supposedly) no easy victims. In this case, taking a more reasonable price in the negotiation seems very logical.

A natural 20 does not make the impossible possible

Your other player seems to assume that a 20 on intimidation makes any foe flee. However, a natural 20 does not make the impossible possible, a check should only be used if a positive result is possible. The possible result here was the goblins dropping their assumption of superiority, not them running away heads over heals.

From a rules perspective, natural ones and twenties are special for attack rolls (always miss or hit; PHB p. 194) but not otherwise (e.g. for skill checks). Of course a GM can apply something similar to ability checks, but RAW this does not happen.

You could more clearly communicate what the expected outcome is

When someone attempts to do something and a skill check is used you can (and in this case you probably should) decide beforehand what can happen. The player attempting the task can describe what the desired outcome is (goblins running away) and the GM can explain what they deem possible, either "yes, that would be possible on a success" or "no, the best you could do would be to make them reconsider the price". That way nobody can be wildly disappointed on a good roll.

Discuss about expectations

To avoid problems it is always useful to discuss what everyone expects from the game. You should ask if the player would be okay if they knew the best they could hope for, or if they absolutely need incredible things to happen on a natural 20. If it is the latter and the other participants cannot accept that, you might have to ask the player to leave. If the expectations are too different that is the only option. But trying to compromise first is almost always worth it.

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    \$\begingroup\$ +1 for clearly communicating the possible outcomes before the roll. A lot of the "Natural 20, so I can do anything" mindset comes from GMs using the die roll as a vague indicator of how much success to give out, rather than setting a DC and sticking to it. \$\endgroup\$ – Mark Wells Jul 17 at 18:09
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    \$\begingroup\$ Thanks, I think this is a great answer you've provided. Actually, after some more discussion between us, we finally stated that the main issue of that day was not this situation (it was the final point). We, as players, failed most of the checks on everything and this final scene might be something that could save a day but it did not. I think this conclusion may better explain what happened on the table. \$\endgroup\$ – Denis Jul 17 at 21:44
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    \$\begingroup\$ I think it’s also good to have a general discussion about expectations. Do you want a game where the player characters are badasses who win (almost) all the time and generally can do as they please? Or do you want a game where you constantly have to run, are short on money, get exploited etc.? \$\endgroup\$ – Michael Jul 18 at 8:19
  • \$\begingroup\$ This is right. Rolls only make sense when there is a possibility of success, a possibility of failure, and success or failure matters. A level 1 rogue trying to casually jump into outer space or a level 2 bard expecting to seduce every tavern wench in the land just isn't realistic, and so a DM should adjudicate immediate failure without a roll. "Your plan to seduce every tavern wench in town with just a smile isn't realistic. If there's a specific one you have your eye on, let me know and we can set up an attempt to woo her specifically. Otherwise your plan fails. What do you want to do now?" \$\endgroup\$ – Robert Columbia Jul 18 at 17:15
  • \$\begingroup\$ A great and clear answer, as a dm I explain to my party that a crit 20 just means guaranteed success not that something amazing happened. Now occasionally for flavor purposes I might have a crit 20 make something special happen in a minor way, searching that room you find a gem worth 150 gold on top of the other stuff, trying to get a better deal on that room you get offered a free extra night after the first 2 etc. but sometimes what the players are trying calls for me to set the dc at natural 20. That player who insists on climbing the sheer castle wall without climbing gear etc. \$\endgroup\$ – Richard C Aug 6 at 22:31
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Natural 20 has no bearing on Ability Checks

The rules for Natural 20 state:

If the d20 roll for an attack is a 20, the attack hits regardless of any modifiers or the target's AC. This is called a critical hit, which is explained later in this chapter.

This is strictly for attacks. There is no such clause under Ability Checks:

To make an ability check, roll a d20 and add the relevant ability modifier. As with other d20 rolls, apply bonuses and penalties, and compare the total to the DC. If the total equals or exceeds the DC, the ability check is a success — the creature overcomes the challenge at hand. Otherwise, it's a failure, which means the character or monster makes no progress toward the objective or makes progress combined with a setback determined by the DM.

So by the rules, just because the player rolled a 20 does not mean they suddenly get their heart's desire. It just means they did the best they possibly could.

Most DMs house rule that the skill check works on a sliding scale. So based on how much you exceed or are under the required DC guides how well you did. So if you only needed a 15, but totaled 23 on the roll/score you might get more than just a pass/fail.

This is a house rule, but it's a very popular house rule. So it's likely that the player feels jilted because they got the 20 when it really mattered but didn't suddenly become master of their domain.

In this case, the DM weighed out everything--number of PCs vs goblins, bargaining chips, environment, the deal that was currently on the table, etc--and made a pretty high DC. But just because they beat the score doesn't negate everything else. The goblins still had the upper hand; with numbers, a hostage, and maybe even a hidden escape route if things went bad. They had no reason to just give up after one good roll.

However, it would not be out of the realm of possibility for that to happen after a number of successful intimidation checks. The first one just made them realize they were biting off more than they can chew. The next makes them doubt their contingency plan. And so on.

So the player just needs to understand the rules and the DM needs to explain what the rolls would accomplish.

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    \$\begingroup\$ "This is a house rule, but it's a very popular house rule. So it's likely that the player feels jilted because they got the 20 when it really mattered but didn't suddenly become master of their domain." OP said that none of the players had ever played before and that this was their second game. Thus while the player in question certainly has a misunderstanding about what a 20N means, it is unlikely that they arrived at this misunderstanding through experiencing common house rules - at least first hand \$\endgroup\$ – Kirt Jul 18 at 22:48
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    \$\begingroup\$ @Kirt, I mean very popular. So even if they have never played the game, it is prevelant in many streams and podcasts. "Because you rolled so high..." is a common phrase so if they watched/listened to games in the past (a good way to get the feel) it is very likely they assumed that since this is how vetern players do it, that must be the way. \$\endgroup\$ – MivaScott Jul 18 at 23:21
  • \$\begingroup\$ As a non-player, I can confirm this is a popular view. I get my information from pop culture (like this, but in fairness, two strips later, the player tries an even more ridiculous trick, and the DM correctly vetoes it on the spot), and the general concept of "natural 20 = You win everything forever" is very widely believed. \$\endgroup\$ – Kevin Jul 20 at 18:43
  • \$\begingroup\$ Just remember, if a Nat 20 is an auto success on any check, then I should be able to punch the moon out of orbit 5% of the times I try. \$\endgroup\$ – aslum Aug 6 at 17:05
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This is what your player is expecting:

Transcript (of chat between "yourplayersaidwhat" and "worddevourer"):
yourplayersaidwhat:
Context: the party is traversing a mountain pass in a blizzard a la Lord of the Rings scene. DM has everyone roll the dice to see if they don’t fall down the cliff, and dwarf warrior in heavy plate armor fails the check.
DM: Heavy gust of wind pushed you off the path. You slip and fall off the cliff. What do you do?
Dwarf: I flap my arms really really hard.
DM: Seriously?
Dwarf: it’s not like I got better options.
DM: ok, roll the dice.
Dwarf rolls natural 20.
DM: ...
Party: ...
DM: roll again.
Dwarf rolls another 20.
DM: ...!
Party: ...?!
DM: ...sigh. With astonished look on their faces, the party behold a most miraculous sight. A dwarf in heavy armor is slowly rising up in the air above the cliff edge by flapping his arms really really fucking hard.
worddevourer: According to all known laws of aviation, there is no way a dwarf should be able to fly. Its arms are too small to get its sturdy little body off the ground. (And aren't wings)
The dwarf, of course, flies anyway, because dwarves don't care what humans think is impossible.

This is not how 5e works (and as a matter of fact, not how most RPG systems I am aware work).

It seems your player is not familiar with the system (it's comprehensible - it's practically their first time playing), and therefore their expectations are completely off from the actual game design.

Talk about these expectations

The system provides a baseline on what the expectations from the players (DM included) should be. That doesn't mean the table can't talk about it and change it if they feel the game will be funnier and more appropriate for them. If you guys can find a middle ground on the expectations for the game, that's the best outcome.

The Rules

Again: the player should be familiar with the book and the rules. There are a few things that the player is messing up here. First, they are completely stepping on DM's territory trying to dictate how the NPCs should behave. That is DM's job. See this related question about DM and players mixing their roles and turning the gaming experience into a very annoying experience (I can assure you the experience was annoying: the question is mine). So, let us remember the basic foundation of the game, described in Page 6 of the PHB, under How to Play:

  1. The DM describes the environment.
  2. The players describe what they want to do.
  3. The DM narrates the results of the adventurers' actions.

Period. The player influences the world through its actions, and some tables may have the players (the real people) be part of the world construction as a whole (Korvin and Nitsua may help you more with that than me), but, ultimately, in D&D 5e, the DM dictates the results of the players' actions, and other than stating their dissatisfaction, the players should not feel entitled to have anything more than that.

Furthermore, the rules are clear on how ability checks work.

To make an ability check, roll a d20 and add the relevant ability modifier. As with other d20 rolls, apply bonuses and penalties, and compare the total to the DC. If the total equals or exceeds the DC, the ability check is a success — the creature overcomes the challenge at hand. Otherwise, it's a failure, which means the character or monster makes no progress toward the objective or makes progress combined with a setback determined by the DM.

Now, the problem here is that the DM and the player had a differing view on what a success means. The played succeeding on intimidating the goblins, which means they have succeeded. But for them, this success should imply on yet another consequence: giving away Sildar for free. This is not the action the player described they wanted to do in Step 2 from How to Play - what they described was intimidating the Goblin. If the player wanted to intimidate the goblins in giving away Sildar for free, that is the description they should have given - and then the DM should not even ask for a roll: just tell them that is impossible, the goblins are not willing to do that, no matter how high the roll is.

In particular, as mentioned in other answers, a nat 20 has no special meaning in ability checks, and, in fact, has a very limited special meaning even in attacks - it is a critical hit, but that is all. No limbs being dismembered (at least not by default - you can include that with some DMG optional rules), no instant kill, no extra anything - just extra dice being rolled in the damage. Going back to talk about expectations, you may decide to house-rule otherwise, if the table agrees, and make nat 20s have special meaning. But keep in mind that it works the other way around - NPCs also roll dice and also have nat 20s, and your players may not like when that happens. In my experience, trying to give special meaning to nat 20s and nat 1s in 5e has always resulted in frustration and has shown to be a bad rule, but that is my personal experience and your table may find otherwise.

It could have been gradual

So, after the first intimidation, the goblins decrease the price. The player (and therefore the character) is still not happy. Why stop then? Continue intimidating, continue bargaining. Roll again. They could further succeed in getting Sildar back for free, or maybe they would roll badly now and fail. Point being: if they are unsatisfied with a result, they can try to improve that result in game, not complaining about it to the DM and saying it's unfair or whatever, and the DM can guide it so the player (and the character) is motivated to try harder and get even more.

Extra comments

Lost Mine of Phandelver is designed for a group of four or five characters, not three. Keeping the encounters as they are is effectively making the campaign considerably harder than it was designed. The 6 goblins are worth 600 Adjusted Experience against 3 level 1 characters, and that is not even considering the HP buff on Yeemik. A Deadly encounter for 3 level 1 characters is 300 XP. And that is happening after the Goblin Ambush, possibly fighting against some Wolves, and the goblin scouts in the entrance of the cave, and, since you already got the frog jade statue, after defeating Klarg (the Bugbear). Thus, you are completely right that the goblins have a huge advantage in this encounter and would probably not be scared easily by only three puny-looking adventurers.

But I am saying that so your DM/GF can keep that in mind: if you guys are running the adventure with 3 players, she will have to re-balance some encounters, or the campaign will be harder than you may want.

Sometimes, Giving in is okay

I will also add this suggestion as someone who has had many problems similar as yours: Sometimes, giving in to the player expectation and allowing them to have it their way, unless it is going to completely break the game by doing that, is completely okay. In this scenario, allowing the players to get Sildar back for free is not game-breaking, and if it was going to keep the table from arguing nonstop with little reason, honestly, I would have done so. I am not saying the ruling was unfair, and I am certainly not saying the ruling was wrong. I am saying that ruling otherwise might have mitigated many problems that didn't need to exist. The player didn't behave the best way either, but it's not the player who is asking the question, it is you, in behalf of your GF, so that's how she can improve: just give in sometimes. Allow the player to feel rewarded.

It's just 40 gp worth of gold. In the next few days you will be getting waay more than that in the adventure. The players don't know it, so they may actually be worried about the gold, but the DM knows, so they shouldn't be worrying so much about it.

Sometimes, it annoys me, as the DM, to give in to something that may not make complete sense to me (like in this case, why the goblins in numerical advantage are scared enough to give up that easily? I don't know), but honestly, it annoys me way more to have to argue with a player for minutes and get people angry, frustrated or leaving the table because of that.

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    \$\begingroup\$ I think a flying dwarf depends on if it's a European or African Dwarf.... \$\endgroup\$ – WernerCD Jul 19 at 3:57
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    \$\begingroup\$ @WernerCD Only its speed depends on such a thing, you fool. \$\endgroup\$ – HellSaint Jul 19 at 14:52
  • \$\begingroup\$ I want to appreciate how the first part of the answer can easily be translated to many other RPGs (as does the question) and only afterwards (starting at 'Furthermore') goes into detail on D&D. \$\endgroup\$ – Rayllum Jul 19 at 21:52
  • \$\begingroup\$ I like the answer, except for the last part about giving in to keep the peace. That is a solution for the moment right now but will lead to far more problems with that player in the future. Either he can learn to accept the DMs authority or he can't but giving in to his demands now just because it's not about much makes him right not to accept whatever the dm says as it is clearly up for debate. What he learns from this is that as long as he's being disruptive and annoying enough, the DM will eventually give in to keep the peace. \$\endgroup\$ – Mark Aug 28 at 12:26
  • \$\begingroup\$ @Mark being clear the suggestion isn't exactly to keep the peace (in the sense "to stop them from being annoying") but rather to allow players to fulfill their expectations when their expectations are not completely out of the feasible, so they can have fun as they imagined. I agree that doing that solely because they are being annoying is not the way to go. It's more an "in hindsight" thing: do that before they get to be annoying. \$\endgroup\$ – HellSaint Aug 28 at 17:56
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Perspective

While there are already many fine answers to this question, they all (currently) give only abstract advice for talking to the player: "Come to an agreement on natural 20s," "Talk about expectations," etc.

These are good answers, with good advice, so no disrespect is expressed or implied. But they're not concrete. My contribution is two specific questions to ask the player:

  1. "If this broke down into combat, how many natural 20s on attack rolls do you think it would take to win the fight?"

  2. "Then why do you think one natural 20 on an intimidate check is going to do it for you? And absolve you of all the hit points, spells, and other expended resources this would require?"

Hopefully the answer to the first question is more than one, or this obviously won't work, but at least you'll understand the true depth of the problem.

And honestly, I've sort of palmed a card with that argument, coming close to the claim that a skill check success should have roughly the same effect as an attack roll success. And that's not true, either. The real precise argument I'm aiming for is not equivalence, but "Surely one of these (skill check) should not be equal to four or five of those (attack rolls)!"

Once that perspective is (hopefully) imparted, then you can start to have meaningful conversations about natural 20s, and skill checks, and how much utility to get out of them, and how many you might need to accomplish a larger goal, etc.

Then you can point out things like:

  • "So really, one roll having the effect of changing the price seems pretty reasonable," or,

  • "Maybe next time, one of them will break ranks and run, but that's completely at my discretion," or,

  • "So honestly, this has to take more than one roll. And I hate just having players make the same roll over and over again, intimidate, intimidate, intimidate. It's boring. How would you have followed that up to get another success?" or,

  • "But this is still a conflict. But now it's a conflict of intimidation vs leadership-- what would have have done if the leader decided he needed to deal with you personally in order to remain leader, and challenged you to a personal fight?"

(This is in accordance with my usual strategy of converting what the players expect to be one-roll successes into longer, more varied challenges requiring multiple successes at multiple skills.)

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Unfortunately, the player was upset, there is no to little you can do with that I'm afraid. However you can prevent issues like this one in the future by setting clearer expectations as the DM.

Come to an agreement on nat 20

Players love rolling natural 20, it feels like a triumph, earlier editions also had special rule for "critical success" for skill checks which could still help players when the DC was too high.

With its "bounded accuracy" principle 5e doesn't have this rule anymore, but many tables still use it, because it feels cool. In the end of the day, we all play to have fun. You might ask your players, if they want such a rule. You should also agree, what does it mean exactly — does it let anyone achieve the impossible, or just yields additional results. When all players agree on this rule, all you need to do is just follow the agreement.

Set the expectations beforehand

Player agency can be defined as an ability to make meaningful decisions, it also implies that consequences usually meet player's expectations (which was the problem, I guess). That doesn't mean there should be no secrets nor surprises. But players should understand what they are capable of, they also should know the cost, risk and possible consequences if things go wrong.

Develop a habit of setting expectations ("what are you trying to achieve?") before asking for an ability check, when it's not something obvious (most social things are not). If your friend knew there is no way goblins let them go for free, (s)he probably wasn't so disappointed by the result. Warn players when they are trying to do something risky.

Expectation-actuality discrepancy could also be a communication problem. In the situation described above your friend probably saw it as safe and felt themselves in control. But in reality it could be quite the opposite — the goblins probably planned to kill everyone, until a lucky intimidation attempt saves the day.

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  • \$\begingroup\$ "Player agency can be defined as an ability to make meaningful decisions, it also implies that consequences usually meet player's expectations" - great quote, and great advice in this answer! \$\endgroup\$ – gszavae Jul 20 at 8:55
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Turnabout is fair play

All of the above answers have good discussion about setting expectations, both moving forward and trying to help the resentful player understand the past situation.

I would just suggest one more thing for trying to help the player contextualize - what if it had been they being Intimidated rather than the goblins?

That is, suppose the goblins had tried to use Persuasion (or Deception or Intimidation) on their character to convince them to betray the party and join the goblins. Would a natural 20 on the side of the goblins have been sufficient to deprive the character of autonomy or acting according to their nature? Would the DM have been justified in saying, "they rolled a 20, you have to do what they say"? In trying to get the player to understand the difference between a natural 20 meaning "you get exactly what you want" and "you do the best you possibly can given the situation", it may help them to realize they may not want to play under the first conditions if NPC's and monsters have the ability to use the same tactics on them.

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    \$\begingroup\$ Would the DM have been justified in saying, "they rolled a 20, you have to do what they say " ? Or, teaching the player that persuasion rolls aren't as strong as magical spells. \$\endgroup\$ – KorvinStarmast Jul 19 at 0:09
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    \$\begingroup\$ +1: Players usually fail to realize NPCs are pretty much PCs for the DM and we want our player agency as well. Obviously we don't get as attached as the players to their PCs, and the PCs are usually assumed to be more special than most NPCs, but it's still DM's territory that they are trying to invalidate there. \$\endgroup\$ – HellSaint Jul 19 at 3:21
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The Right Time for Roleplaying

The accepted answer is wonderful; GM's should absolutely ask a player to state their intention when it's unclear what is expected. I would add one more thing I noticed when reading your question:

but my friend decided to intimidate them, roleplayed and rolled a natural 20.

I've had great results in managing player expectations by asking players to roleplay an action only after the GM has told them what the consequences might be if they succeed or fail.

Whether that roleplaying happens before or after a roll: a player knowing what the consequences are can incorporate those outcomes into their player fantasy before they spend too much time developing that fantasy, thereby preventing a disconnect between the player's roleplaying and the reality of the dice roll.

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