She said he didn't owe her it, but somehow he felt like he did. If they were all going to be living here he didn't want things to be bad between them. Dean didn't have many people in his life, and he liked Jo. She understood the kind of life him and Sam led and didn't think different of them for it. And even now, knowing where he had gone she was still there, sure it was a little weird and awkward but she wasn't running for the hills.
He shrugged a little. "I don't know, maybe I do, maybe I don't. But either way I am, sorry." He looked to her beside him and smirked a little. "Not that I'm entirely sure a better way for that conversation to play out," he admitted. Was there even one? He kind of doubted it.