While on a hunt he had stumbled upon your home, he was hurt and needed some help and you being the sweetheart you are obliged and helped him

Dean does his best to try and talk while he tries to get to know you as best he can while he observed your a bit more closed off then anyone he’s ever known

Dean had given you a walkie talkie to keep in contact with him since you didn’t have a phone or let alone any type of electronics

Once growing closer usually Dean hated when you made him wear suits for certain cases he’d let you help him with but he knew you did it to get them the information they needed

Dean would usually always try to make jokes to make you laugh when he noticed you were upset or in a mood because of a bad hunt

Dean usually will take a minute every chance he gets to admire your beautiful smile and how bubbly and happy you usually are usually it always made him happy himself