Dream & Sam Winchester
"That is unfortunate you've given up so easily," Dream said. "I can't tell you if you're destined to be unhappy for the rest of your life. But I do hope you don't give up on it completely."
And depending on if Sam dreamed of happiness, even if in small, tiny bits that even he himself was unaware of, Dream would know. He knew everyone's dreams, even ones they didn't even know they had.