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Players get frustrated when they couldn’t solve a hard diplomatic problem, how to get them to think out of the box

Problem:

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 with 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, and 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 they did not enjoy the session. Player enjoyment is my top priority. But I also think dnd 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:

P: If trying to out smart a bad person with a lot of influence in the town

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.

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 exp, still got some loot, and got some more plot).

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