We’ve discussed both versions, because honestly they’re all too cute! There’s no way of knowing what’ll happen until we get there, but there’s a good chance that Dean will terrify Oscar as usual XD Kiddo Sam would rescue the tiny kiddo from his big brother, and Dean would be trying to peek around his shoulders to see what’s going on.
The adult Winchesters are much more scare and it might be a while before Oscar even tries to uncurl from his Oscar-ball ^^;
Hopefully they’d discover that a quicker way to his heart is to give him food and to be hands-off at least at first. Oscar’s only ever heard about how bad humans are, after all! He is very little and they are very big, and the Winchesters are extra big. Just gotta give him time (and maybe pizza).