It does feel good, in a way that, despite everything he's just said, he wasn't expecting. He's been held before, he's had someone else's face this close to his, but there's always been that tension in his shoulders, that readiness to fight and flee if things go wrong. But right now, that twinge of fear is gone.

He leans into the side of Rosi's head, closing his eyes. It doesn't quite occur to him that the appropriate thing to do would be to return the hug— it just isn't a gesture he associates with expressions of genuine affection. Mostly because he doesn't associate much of anything with expressions of genuine affection.

"If it makes any difference, I don't think either of us really knows what we're doing." Perhaps that's assuming a lot, though now that he thinks about it, Will realizes he doesn't actually know all that much about Rosinante's romantic past. Maybe he's had tons of relationships. It seems unlikely, though, seeing as how they're both just sort of grasping in the dark.

"How long have you... ?" Had feelings? Known this was different? He wishes he had the courage to name this. Would make referring to it a lot easier. "How long have you been keeping this to yourself?"