Tim knows enough to call them "cryptids", so he's obviously not as dumb as he says he is. He knows more than he's letting on. Jay's less sure whether or not he knows anything relevant, but that's the next step.

Tim didn't outright deny he got lost after his so-called "fall". It's risky, but Jay decides it might be worth trying to call his bluff.

"Yeah?" He jerks his head back toward the trail. "At least I know the way out."