Would it have really made a difference if Bobby had told Dean about Littles before he encountered Sam at Trails West? In other words, would they still have met and, if they did, would it have been at all similar to their meeting in Brothers Apart?

It definitely would!

Dean would still be jumpy if he ran into Sam without warning, but he’s also not about to bother a person just minding their own business getting supplies. He’d be more likely to let them go and see if they knew anything about the problems Trails West has been having, since borrowers/littles are a very good source of information for the hunters that protect them.

So they would definitely still meet, Dean would grab Sam, let him go, probably with a warning that something’s up in the motel, and Sam wouldn’t be able to resist giving Dean a hand with it, only to discover just who Dean is in the first place. 

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