Awwwwwwww. Also I'm not sure if it is but I've decided it's Gabriel from Supernatural.
Supernatural. Character study: Gabriel
Supernatural // Gabriel // Trickster // Richard Speight Jr
It's just so Gabriel to be all "What is the most awkward way I can get this information out? Preferably scarring these two for life. (Ooh maybe Cassie'll have to see it! Oh this is sooo happening.)"
Supernatural - Gabriel. i miss you my little archangel.
Supernatural fandom More
Supernatural Harry Potter Crossover Sam Dean Winchester Gabriel Castiel
supernatural gifs | supernatural gabriel trickster supernatural gif
Lol, I Love That Behind Dean, Sam Looks Pissed. No One Tells Sam's Angel To Bite Them, Except Sam. XD