You knew about Cassie. Dean's first love. Of course, you trusted him, so what did it matter to you who he had loved before you? It didn't matter to him. But it was a little awkward when the three of you hopped in Baby to go help Cassie with some weird shit that was happening in her hometown. What was even more awkward was when Cassie had hugged him despite seeing you holding his hand, and had looked directly at you while doing so. It kept happening. She'd touch him…look at him like she wanted him still…look at you like a bug despite Dean constantly praising you. Yeah…Dean didn't like that. He'd wanted to see her, to be friends and maybe get some closure for past mistakes but it seemed like she thought they were going to pick up where they left it and Dean really didn't feel comfortable with that.
"Listen, Cassie. You're a great girl and I'm real happy you called."
He sighs. glancing at you and Sam talking to make sure you were out of earshot.
"But I have my girl now, and nobody can replace her…ever. Those feelings I used to have for you? They're not there."