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KAI when he returns from the prison world that you'd trapped him in. You were his escape plan but you ended up getting out without him, knowing that if he got out then he'd wreak havoc on all of Mystic Falls.
"Did you miss me Y/N? I missed your pretty face." "Kai, how the hell did you get out?" "Just the usual, struck a deal with some Heretics. Hey, are you still single? We should grab some dinner after I kill all of your friends"
