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Ron and Draco
Both were raised in pureblood families and had a lot to live up to. Draco because he was expected to be exactly what his family wanted him to be, and was an only child, so he had to be perfect. Ron because all of his older siblings, even Fred and George, had done so many great things.
Both were at times under appreciated. Ron was the last boy in the family, and all of his older siblings had done so much that, until he got his prefects badge, he didn't seem to get much attention. How else do you explain the fact that Molly knitted him maroon sweaters when he hated maroon or the corned beef sandwiches, which he also hated. Draco was forced into being a Death Eater because of his fathers incompetence, without any consideration to him. He was treated as though he didn't matter.
Both had to live up to impossible expectations. Ron was expected to become as good as his siblings, which was a ridiculous considering what all of them had done. Draco was expected to kill Dumbledore, something that Voldemort himself couldn't do.