[RPG] Players get frustrated when they can’t solve a hard diplomatic problem. How to get them to think out of the box

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My players got themselves into a diplomatic problem that they know is probably above their pay grade in terms of difficulty. They spent a session trying to figure out this problem by talking to people, and rolling different Charisma checks in order to try to persuade people they probably had no business persuading (rolls were average, arguments weren't extremely compelling). The party didn't plan any grand schemes, any extraordinary strategies, no clever ideas on the spot, but rather tried very basic head first dialogue.

This has happened in the past in regards to combat. The party has (with a recent deadly encounter) had to think out of the box more (one player even said: "guys we need to plan more and think less about just hacking and slashing sometimes"). Now it's a more diplomatic problem that doesn't seem as easy as rolling a single Charisma check and hoping it works out.

In the end, the party did not manage to solve the diplomatic problem (although there is room in the future for them to try again with the upper hand), and one of the players said that they did not enjoy the session. Player enjoyment is my top priority. But I also think D&D is best when there's risk, when you can fail rolls, when the PCs don't always win (not that I actively seek this out though).

How can I get the party to perform less linearly in dialogue-related problems?

An example problem at our table:

Problem: If trying to outsmart a bad person with a lot of influence in the town

Answer: There are options for framing the person, bribing people, seeking dirt on this person to find their weakness, tarnishing their reputation, trying to prove their wrong doing by seeking out evidence, and a bunch of other possibilities.

I've tried to have a brief session-0 talk again about if they want dialogue-related problems handicapped, and they didn't seem to take to that, but rather felt like they tried everything and didn't know what else to do. I also did a postmortem on this problem and tried to give different options they could have tried, but I get a feeling the players feel like they still tried everything and failed and the session was "a waste" (even though they still got XP, still got some loot, and got some more plot).

I'm kind of at a loss of how to tackle this issue that isn't just: "Go watch some D&D podcasts to get ideas, or go read X, Y, and Z resource on the subject".

Best Answer

A: There are options for framing the person, bribing people, seeking dirt on this person to find their weakness, tarnishing their reputation, trying to prove their wrong doing by seeking out evidence, and a bunch of other possibilities.

Did you tell them this?

Did you tell them the pros and cons of each option?

I don’t (necessarily) mean straight out enumerating the options you see (although I have done this) but you need to have scenes where these clues (at least three for each option) get from your head to their head.

Role playing is about making choices but you, the DM, are the source of all knowledge in the world and what’s obvious to you is never obvious on the other side of the screen.

Players that are throwing out imaginative ideas and making progress are having fun. Players who are going around in circles and not making progress aren’t. From time to time part of the fun of DMing is schadenfreude but it’s best in small doses.

When they get stuck - give them a push.