I'm guessing it's because he tries to dream about something, but each time he's unsuccessful, he just expects to be more unsuccessful.

I mean, when he asked you a question, he said it himself that he "doesn't dream about something" he wants to. If he expects to fail, why would he succeed?

Either way, to dream specifically about something, I'd suggest something like MILD. But if you're doing MILD anyway you might as well try to get lucid.