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He wonders about when she will leave him.
All the others did, after all. Lucifer left first, the hardest break for their father; others left along the way, like his sister who fell. He can't think of the Winchesters without remembering every little hurt, all the greater for being experienced with a human heart.
So he can't help it, looking at Kaylee and thinking that someday this will all be over. Someday she'll look right past him without stopping. She won't smile when he walks in the door or be there in the middle of the night to throw her arm over his chest and mumble something that only makes sense in her dreams.
This would never have crossed his lips but one night, when he's been back for about a week, she gets him good and drunk. Almost he suspects her of devious purposes in doing it, but he can't quite believe that of her. Even so, he finds himself talking, words falling over his lips from a tongue that feels too thick, and suddenly her eyes are wide and her lips are pressed together and pushing up into a pout, and he thinks that's what she looks like when she's trying not to cry.
Then she smacks him on the shoulder. It doesn't hurt but he'll find a bruise there tomorrow.
"You're the one that left, genius," she says. "You don't get to ask when I'm leaving. 'Cause I'm not."He thinks that this made more sense in his head, before the bourbon, before she pulled him out of his chair and up to her bedroom. But it's hard to think of his reasons, to think of why he's meant to be alone, when she's soft and warm and yielding under him in the darkness. It's hard to think about falling or flying from anyone's arms when she has hers so close around him. And it's hard to think about loneliness and fate when the sound of her breath is lulling him to sleep.