Yikes. That story about the boy...
I think some people block themselves from strong negative emotions (often because of a traumatic childhood), and this causes them to have limited ability to really feel what another person might feel in a bad situation. Of course you can experience pleasure when you gain at someone else's expense, but how would they feel? When you're blocking negative emotions, you're also blocking the positive ones like love.
Sure, the universe will let you be a jerk - beautiful thing that free will is. But what I have learned is that on the one hand is pleasure (from getting some materialistic thing you wanted, or power, or whatever), and on the other hand is happiness. A sense of internal peace, a clear conscience, feeling the joy of someone else. Pleasure is very transitory. Happiness can be much longer lasting. Not saying pleasure is bad - it's good - but not at the cost of integrity. Sorry if I'm sounding a bit puritan here, I'm not trying to pretend I'm perfectly righteous or anything. But yeah, give the $50 back.
..Back on topic: Yes, that would be wrong. Why? Because it's not respecting the other person's boundaries. If you ask me, I say let them find their own path and face their own fears. If you want to help them, ask their permission first. It's not about whether or not you would enjoy or appreciate nightmares. It's about if they would appreciate them. Respect their choice to take a less courageous path (even if it is the wrong path, like, in the case of bad morals )
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