One Day Toothless is wondering through the woods, while Hiccup looks around for him knowing Toothless is planning on pouncing on him to scare him, which doesn't scare him anymore but it's worth a shot I guess

/Hiccup/ "I wonder where Toothless must have gone?" he says, tapping his chin playing along with Toothless' antics like a big brother

But as Toothless was about to Pounce onto Hiccup from the bushes, he sees someone in the distance quietly wondering...and you catch his eye as he's now curious of who's there and very cautious...