Sam had earlier said that killing Amy was wrong because “if something feels wrong, it probably is!” Dean countered that while this was usually true, killing Amy was not wrong. In their final conversation, Dean justified his killing of Amy by saying, “I went with my gut. And that felt right.” Then Dean said that lying to Sam didn’t feel right. This implies that Dean is agreeing with Sam's earlier statement.
I took that as Dean saying that lying to Sam was wrong. I'm still at least 50% sure that's true.
But what if it isn't? Because Dean doesn’t actually say that. He says it makes him feel terrible, which within the context of that conversation implies that he thinks it was wrong. But he never says that, nor does he counter his earlier claim that lying was “reasonable”.
What if something making you feel bad implies that it’s the right thing to do?
The righteous man who tortured souls in Hell.
What if Dean's world, making you feel bad is a sign that something is the right thing to do?
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