John Gilbert is extremely shady. He was always known to Elena and Jeremy as "Uncle John"; however it becomes known that he is actually Elena's biological father. He hates vampires and does anything he can to protect Elena from them.
At the end of season 2, John sacrifices himself to save Elena. He also writes her a letter apologizing to her for everything he did in the past, and leaves his protection ring for Elena to give to her future child.
You want a love that consumes you. You want passion and adventure, and even a little danger... I want you to get everything you're looking for. But for right now, I want you to forget that this happened. Can't have people knowing I'm in town yet. Goodnight, Elena.Damon
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Hey, Blondie. Today isn't the worst day of your life. Today and tomorrow, it's a cakewalk. There'll be people around you day in and day out like they're afraid to leave you alone. The worst day? That's next week when there's nothing but quiet. Just a heads up.Damon