Young Dean and a Girl - Supernatural Season 15 Episode 16
On Supernatural Season 15 Episode 16, Sam and Dean are asked to investigate the murder of a childhood friend, a case they thought was solved a long time ago.

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Bettina Strauss/The CW
Supernatural Season 15 Episode 16: "Drag Me Away (From You)"
Sam Winchester, Dean Winchester
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Supernatural Season 15 Episode 16 Quotes

Caitlin: Hey, that thing. Were you scared?
Dean: Always am.
Caitlin: You HAVE changed. The old you never would have admitted that.
Dean: I'm not sure that's a good thing.
Caitlin: I think so. What do they say about getting older? You tell the truth more because you know that lies, they don't make anything better.

We barely go to school, so if you think some place like that is going to let a dumbass like you in? Come on. This, Sammy, this is our life.