Harry didn’t like that "should.’ He didn’t know how seriously Riddle was still considering Dark Lord-dom, and Riddle wouldn’t give a definitive answer. He hoped it was because Riddle truly wasn’t sure, and not because he refused to give Harry knowledge to use against him, since Harry wasn’t sworn to secrecy about anything Riddle did in this life. "Well we’ve got almost two years until we graduate. Plenty of time to work on those connections."