Dean and Bobby Loran would be the worst mixing of characters, especially a smol Dean with Bobby. Someone’s gonna get hurt if Jacob isn’t there to help.
Considering in the motel sprites au Jacob’s friends at least know about sprites (and they know he Will Punch someone who threatens them too much), they might hesitate. Chase would definitely be more chill about it, and most likely just heckle Dean with innocent teasing. Bobby Loran, though, even if he’s learned a thing or two about respecting smol folk, needs to be watched more closely.
Of those three human dorks, Bobby would be likely to learn Dean’s mantra of “You grab, I stab” very quickly. For once it’s not Jacob getting slashed.