Caroline Forbes: You shouldn't leave again.
Tyler Lockwood: You're kidding, right? This is the second time I've tried to kill you.
Caroline Forbes: Well, no friendship is perfect.
Matt Donovan: [to Caroline] I get it, this is your life now. But you know what my life is, Car? My life is an absentee mom, and a bunch of bills to pay, and school, and a job, and it sucks sometimes, but it's my life and I think that I just want to live it without all this.
Katherine Pierce: One hundred and forty-five years and no last goodbye?
Damon Salvatore: You don't get a goodbye.
Katherine Pierce: Don't-don't leave mad.
Damon Salvatore: Us ending up on good terms is not exactly on my bucket list, Katherine.
Katherine Pierce: Klaus made me call Jenna to lure her out, there was nothing I could do, I didn't have a choice.
Damon Salvatore: That's why I gave you the vervain, so you *had* a choice.
Katherine Pierce: It was her or me, I chose her.
Damon Salvatore: I helped you, you owed me. Now when Klaus dies, you're going to walk out of here without a scratch, and Elena's aunt dies. Sometimes you're the only one that wins, how'd that happen?
Katherine Pierce: I didn't let love get in the way.
Damon Salvatore: Enjoy eternity alone, Katherine.
Elijah: You're very honorable.
Stefan Salvatore: Are you? Because this plan is contingent on your honor, Elijah.
John Gilbert: You ruined her life. You know that, right?
Damon Salvatore: I know that, John. I took her choices, destroyed her future, I get that.
John Gilbert: [John's final letter to Elena] Elena, it's no easy task being an ordinary parent to an extraordinary child. I've failed in that task, and because of my prejudices, I've failed you. I'm haunted by how things might've played out differently if I'd been more willing to hear your side of things. For me, it's the end. For you, a chance to grow old and someday do better with your own child than I did with mine. It's for that child that I give you my ring. I don't ask for your forgiveness, or for you to forget. I ask only that you believe this; whether you are now reading this as a vampire or as a human, I love you all the same as I've always loved you, and always will.
Damon Salvatore: Her soul? Really? You're going to put some faith in some act of God mumbo jumbo?
John Gilbert: I refuse to let Elena become the thing I spent my life protecting her against, and you can call that God, or mystical energy, or whatever you want, but yes, I'm putting my faith in it.