"And... I'm gonna need you take care of me afterward."

There. He said it.

"Like—I don't know. Be there. Be... safe. Probably let me cry on you a little."

He's trying not to ask for things Obie can't give him, but this would be so much easier with Sherry. With Sherry he'd just say, love me?, and Sherry would say Always, and that would be that.