That's the expression he was hoping for. This is familiar, for them, a memory of good times and good feelings. And he's pretty sure he can do it. Like HYDRA, prison guard pirates weren't particularly focused on hair except occasionally to pull.

B sinks onto the couch at last, himself, half-turned against the arm, and pats the cushion next to him. Not too close, hopefully, but where he can get at her hair.