Dean was the star player and captain of his high school baseball team, so it was his job to pick and chose the new recruits for said baseball team.

During baseball tryouts, Dean had seen you walking around with Sam and pulled his brother aside.

"Damn, where have you been hiding that?" He asked. Sam rolled his eyes, "don't even try dea-" before he could finish Dean was already walking over to you.

"So, you here for tryouts?" He asked, looking you up and down, obviously checking you out.