You'd never seen Dean so caring towards someone before. It broke your heart a little, cause you always thought he cared for you as much as he possibly could. But one look or mention of Lisa Braeden completely left you in the dust. Dean had dropped everything to stop by and see her after 8 years of no contact. You barely even saw him that weekend, even though you were literally working a case together at the same time. Once it was over, and he'd kissed Lisa goodbye, you were gone, and Dean knew he fucked up big time. The two of you weren't dating yet, but he wanted to date you so bad, wanted to try to have a long-term relationship so bad. Dean had feelings for you for years when you started hunting together, and he knew that if anybody was his soulmate, it was you. But dammit he wanted to see Lisa. He hadn't meant for it to be romantic in any way, and it really wasn't in his eyes until Lisa kissed him goodbye but… it killed him when he got into the impala with Sam and looked into the backseat to not see you. Sam told him you'd taken off the night before, and Dean knew damn well you had probably gone to Bobby's. So that's where he headed.