Dean had only been in love with one person in his life- you. And he lost you.

You and Dean met when, Sam- deans little brother ran off to Stanford. You were a hunter like Dean. You helped Dean on some hunts, you were great company.

Dean fell in love with you, it wasn’t quick. It built up over time, it snuck on him before he could stop it. He truly loved you so much it hurt. You started dating, you dated for about a year. It was probably the happiest year of deans life- and he knew that.

Dean knew what his life was, he put people in Danger, he couldn’t save everybody. He didn’t want to lose you that way. So he let go of you himself, pushed you away. He said it was for the better. That he was protecting you.

It’s been about 2 years since you broke up. You two haven’t spoken, but the silent yearning was there. Dean regretted every decision he made with you, he should’ve never let you go- but he couldn’t put you in danger. He wanted you so bad. But you were gone now. He ruined it a long time ago.