Opinions?
I've been bugging myself about this, and I can't make a decision. So, oh wise friends, I appeal to you.
Scenario (consider it AU, if it helps) pre-series or season 1:
Sam and Dean are spending a couple of days with a group of Sam's college friends. It's a full moon night, everyone's a bit drunk, and they're telling "ghost stories" - this was not Sam or Dean's idea. As far as they know, no one in the group who isn't a Winchester has a clue that all this stuff is real and ghosts can really hurt you.
When it's Dean's turn, would it be in character for him to tell them a true story about a real hunt (given that he expects everyone to assume it's fiction)?
I can't decide. Anyone?
Scenario (consider it AU, if it helps) pre-series or season 1:
Sam and Dean are spending a couple of days with a group of Sam's college friends. It's a full moon night, everyone's a bit drunk, and they're telling "ghost stories" - this was not Sam or Dean's idea. As far as they know, no one in the group who isn't a Winchester has a clue that all this stuff is real and ghosts can really hurt you.
When it's Dean's turn, would it be in character for him to tell them a true story about a real hunt (given that he expects everyone to assume it's fiction)?
I can't decide. Anyone?

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You think it would work? Cool! :D
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Now, tbh, I've only seen part of season 1, so... take this with a huge grain of salt. XD
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I think the difference is Dean would tell his story in the first person, if he's relating true events. Others might tell a made-up story that way, but would be more likely to use third person. You have to be used to (fictional) storytelling to adapt in that way and I don't think Dean would. You're right...if he can embarrass Sam while he's doing it, he wouldn't be able to resist that :)
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Well...no one seems to think he wouldn't do it. So I guess I have my answer. Thanks!