Dean comes back from his week-long solo trip kind of shell-shocked, but Sam doesn't get the chance to drag it out of him before Castiel shows up in Dean's dream and everything goes sideways.
They're busy with Jimmy Novak and his family, and then Sam spends a few days going out of his mind while he's detoxing. And then, of course, there's the disaster with Ruby and Lilith and Lucifer.
He hates himself for it later, that he forgets.
Wendy doesn't see Dean again for another year.
(Although, a few weeks after he leaves a guy in a trench-coat appears suddenly in her living room and slams his palm into her chest. While she's still gasping for breath, he does the same thing to Hanna, who starts screaming. Then he says, "Lucifer walks free. I have made it impossible for you to be found by supernatural means," and disappears. Before she can panic enough to take Hanna to the hospital, she finds a letter on the table, addressed to her in Dean's handwriting, which tells her little more than Trench-coat guy, who turns out to be Castiel. Dean just uses more words.)
When he finally does show up, it takes Dean two weeks before he can bring himself to tell her why he came back alone.
After that, he disappears into a bottle and doesn't come out for a month.
He doesn't expect it (at this point, the only thing he expects is Wendy kicking him out), but when he thinks about it later, it isn't very surprising that it's Hanna who saves him.
He wakes up one day, already reaching for the bottle he didn't quite finish yesterday, to find her sitting on the floor in front of him. He pauses to squint at her and, apparently seeing that he's no longer asleep, she hands him a sheet of paper. He sits up to take a closer look.
"Hanna," she says, pointing at the smallest stick figure. "Mommy," she continues, pointing at a larger stick figure, which is holding hands with the first.
"Daddy," is larger than Hanna and Mommy, and he's crying.