“Harry couldn’t explain, even to himself, why he didn’t just throw Riddle’s diary away… And while Harry was sure he had never heard the name T.M. Riddle before, it still seemed to mean something to him, almost as though Riddle was a friend he’d had when he was very small, and had half-forgotten.” – 233-34, CoS
There are a couple of reasons that this paragraph has intrigued me since I first read it. First and foremost, the emotional reaction or feeling that Harry has for Riddle is POSITIVE. It is the same type of feeling/emotional response one would have for a friend. Harry even seems to think that Riddle may have been a friend at one time – even though Harry can’t logically see how he could have been. Another intriguing aspect of this paragraph is that Harry feels as though Riddle may have been a friend when Harry was very small, but Harry seems to have “half-forgotten” him. If Harry has half-forgotten Riddle, then he also half-remembers him. I think that this indicates that Harry must have had some positive connection with Riddle between the time of his (Harry’s) birth and when Harry finds the diary. Some might argue that the connection between Voldemort and Harry – resulting from the attack – would explain the relationship, but I disagree. For one thing, Riddle was going by “Voldemort,” and it is the name “Riddle” that Harry was remembering. Although I have no theories as to how all of this took place, I do have a theory as to how it will affect Book Seven.
There have been guesses as to how Harry will kill Voldemort, but I don’t think he will. As we saw from our hero in Book 3, he was unable to kill Sirius when he thought that Sirius had betrayed his parents, and he was unwilling for Remus and Lupin to kill Peter – even though he may have deserved it. I don’t believe that Harry is capable of murder. He might vanquish (overcome in battle) Voldemort, but he may befriend Tom Riddle.