– Every time you speak, Jack would be hanging on every single word.
– He would be wearing the brightest smile when he sees you or hears your voice.
– Jack would be insanely protective of you, just as he is with everyone he cares about.
– He would be unsure of his emotions, he wouldn’t know or understand what it is that he is feeling for you.
– Dean would try giving him advice on how to tell you and ask you out, only for –
– Sam to be horrified by what Dean said and then give Jack better suggestions.
– Jack would always be bringing you your favourite candy/chocolate.
– Jack would always be watching and admiring you from a distance, he thinks you’re the most gorgeous and captivating human to exist.
– Jack would always be talking to you.
– Him feeling safe and at home when he’s around you.
– When you catch his eyes on you, Jack would get shy and he’d blush a bright red too.
– He would always come to you for advice because he trusts you more than he trusts anyone else.
– Jack would finally tell you he likes you one day as you two are walking through the forest outside the bunker. He would pull you to a stop, his hands intertwined with your own, and confide his feelings to you.
Toad's Cave 