You and Dean were dating for a long time. You both met when you were kids and the relationship grew from that. You fell in love but you fought a lot, which led you to pay for it in the middle of a fight.

Your father and his were friends so it was inevitable to see each other sometimes since you hunted together, you helping yours and he helping his. Although you felt some longing for each other you still hated each other a little because your personalities didn't match.

Approximately a year passed and Dean's father had disappeared. Dean looked for Sam and they both went to look for him. Sam was going to go back to college but unfortunately something strange had killed his girlfriend, now the young Winchester with a broken heart wanted to look for what killed his girl, although John's case was still standing. One day both brothers were in another state investigating another strange case. They were at the crime scene, they had been left because they were wearing fake police badges. Dean looked at the scene with Sam until he looked up and saw you. You were there too, probably doing the same thing as them, he could recognize you instantly and his heart froze so much that Sam noticed it

—"Hey Dean... Are you okay?"—

Sam said somewhat worried and looked up where you were and saw you, he understood everything

—"What is she/he doing here?"—

Dean said with a slightly confused tone, it seemed like longing and anger was awakening