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How to make a choice more sadistic?

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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?

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Few realistic choices are that hard in themselves. What makes them hard is history.

Does Spiderman save Mary Jane or a bus load of schoolkids?

Easy, save the school kids. The needs of the many, etc.

But wait, Spiderman is in love with MJ.

Yeah, but still, 30 kids on that bus...

But wait, Peter Parker has been in love with MJ for years. He has pined for her as she has dated bullies with fast cars. Finally after years of pain and waiting he has won her over.

And now the decision is much harder to make, is felt much more deeply, both by that character and by the reader.

All effects in fiction are created by the right setup, not by how you tell it in the moment, but by everything that has gone before that brings the protagonist to this moment of truth. Reflect on just how long the movie spent on setting up Peter loves MJ before putting him on that bridge with the bus in one hand and MJ in the other. It is all about setting up just how gut wrenching that moment is going to be for him.

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The toughest dilemmas I have faced are the ones where I spin my wheels, going around and around because of doubt. So you have to set it up in such a way that there is no satisfactory choice.

The common approach to the situation you described in your pre-edit question is for Ed to be highly motivated for the sting operation to take place, in order to catch someone Ed truly loathes; but at the last minute he discovers that his younger brother or childhood friend is going to go down with the big bad guy if the sting operation proceeds as planned.

Or you could have the police officer getting credit for the sting operation be a hypocrite who will personally benefit. This would give you some Chandleresque bitterness.

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