Sam: Dean, is it really you?
Dean: Yeah, it's really me.

Rule number one, you can't have a trap without a bait.

Dean

I hope someday to have a little bit of her hope and courage.

Jack

Why be the hunted, when you can be the hunter?

Dean

You know, in all my thousands of years what happened to Jimmy Novak and his family, it's my greatest regret.

Castiel

You know what's difficult? There's no evidence.

Nick

Did you really think I didn't know what you were? I picked you. Now summon your master.

Dean

Lucifer may have inflicted more damage on your psyche then we expected.

Castiel

That's doesn't make any sense, Sam. I've never heard of an interaction between archangel and a vampire -- certainly not in this universe. And why would Michael be killing them? I mean, they're not a threat to him.

Castiel

Dean: Get out!
Michael: Oh, I don't think so.
Dean: You can't!
Michael: Oh, but I can. You see I own you. So hang on and enjoy the ride.

Castiel: Jack, mourning what you've lost is wasteful. It might be smart to focus on what you still have.
Jack: You don't understand what I'm going through.
Castiel: Yes I do, a little. At the time of the great fall when the angels were banished from heaven, I lost what I thought was everything. I had not grace. I had no wings. I felt hopeless and useless.

Castiel: Looks about two centuries of biblical lore. Light reading.
Jack: Researching how long it takes archangel grace to replenish.

Supernatural Season 14 Episode 2 Quotes

Who goes to Duluth in October? You sure Michael didn't touch down in Orlando?

Bobby

A little of this, a little of that and yes, good boy. Hmm. Too much that. Disappointing.

Dean