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Source: https://writers.stackexchange.com/q/26444
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

How do I create an impossible choice for my protagonist? I want to place him in a painful dilemma, and I'm having trouble making the choice feel truly impossible.

For example, I'm writing a scene where store owner Ed learns of an upcoming sting operation at his store. Ed is friends with both the cop running the operation, and the customer who's the intended target, so I thought that could be developed into a good flashpoint, torn between two friends and dangerous circumstances.

The problem is, it's not really _that_ awful a situation. He has an easy option -- alerting the customer and canceling the drug deal -- that may be unpleasant (e.g. his cop friend is embarrassed in front of his captain; the drugs stay on the streets), but is still _much_ better than the worst-case scenario -- a friend going to jail, and his store made famous as a location for drug dealings.

How do I take a scenario that's unpleasant, but has a good answer, and turn it into a really awful, painful, sadistic decision the protagonist has to make?

Original score: 3